CH618154A5 - Process for the production of substituted benzhydrols - Google Patents

Process for the production of substituted benzhydrols Download PDF

Info

Publication number: CH618154A5
Authority: CH; Switzerland
Prior art keywords: lower alkyl; condensation; general formula; tetramethyldiphenyl; radical
Prior art date: 1976-01-14

Application number

CH46777A

Other languages

English (en)

French (fr)

Inventor

Michel Vincent

Original Assignee

Science Union & Cie

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1976-01-14

Filing date

1977-01-14

Publication date

1980-07-15

1977-01-14 Application filed by Science Union & Cie filed Critical Science Union & Cie

1980-07-15 Publication of CH618154A5 publication Critical patent/CH618154A5/fr

Links

238000000034 method Methods 0.000 title claims abstract description 18
QILSFLSDHQAZET-UHFFFAOYSA-N diphenylmethanol Chemical class C=1C=CC=CC=1C(O)C1=CC=CC=C1 QILSFLSDHQAZET-UHFFFAOYSA-N 0.000 title claims abstract description 15
-1 alkyl formate Chemical compound 0.000 claims abstract description 22
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims abstract description 14
238000009833 condensation Methods 0.000 claims abstract description 9
230000005494 condensation Effects 0.000 claims abstract description 9
150000002680 magnesium Chemical class 0.000 claims abstract description 5
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims abstract description 4
125000003545 alkoxy group Chemical group 0.000 claims abstract description 4
125000000217 alkyl group Chemical group 0.000 claims abstract description 4
229910052731 fluorine Inorganic materials 0.000 claims abstract description 3
125000001153 fluoro group Chemical group F* 0.000 claims abstract description 3
239000001257 hydrogen Substances 0.000 claims abstract description 3
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 3
LFAGQMCIGQNPJG-UHFFFAOYSA-N silver cyanide Chemical compound [Ag+].N#[C-] LFAGQMCIGQNPJG-UHFFFAOYSA-N 0.000 claims abstract description 3
229940098221 silver cyanide Drugs 0.000 claims abstract description 3
ZDVDCDLBOLSVGM-UHFFFAOYSA-N [chloro(phenyl)methyl]benzene Chemical compound C=1C=CC=CC=1C(Cl)C1=CC=CC=C1 ZDVDCDLBOLSVGM-UHFFFAOYSA-N 0.000 claims abstract 2
OKFOGGVYBGIWSE-UHFFFAOYSA-N bis(2,6-dimethylphenyl)methanol Chemical compound CC1=CC=CC(C)=C1C(O)C1=C(C)C=CC=C1C OKFOGGVYBGIWSE-UHFFFAOYSA-N 0.000 claims abstract 2
239000012320 chlorinating reagent Substances 0.000 claims abstract 2
239000000203 mixture Substances 0.000 claims description 12
WEVYAHXRMPXWCK-UHFFFAOYSA-N acetonitrile Substances CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 11
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 5
239000002253 acid Substances 0.000 claims description 5
239000011777 magnesium Substances 0.000 claims description 5
229910052749 magnesium Inorganic materials 0.000 claims description 5
125000001424 substituent group Chemical group 0.000 claims description 5
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 4
WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 claims description 4
TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 claims description 4
239000002904 solvent Substances 0.000 claims description 4
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
239000000460 chlorine Substances 0.000 claims description 3
229910052801 chlorine Inorganic materials 0.000 claims description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
238000002360 preparation method Methods 0.000 claims description 3
HXKKHQJGJAFBHI-UHFFFAOYSA-N 1-aminopropan-2-ol Chemical compound CC(O)CN HXKKHQJGJAFBHI-UHFFFAOYSA-N 0.000 claims description 2
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 2
WZKSXHQDXQKIQJ-UHFFFAOYSA-N F[C](F)F Chemical compound F[C](F)F WZKSXHQDXQKIQJ-UHFFFAOYSA-N 0.000 claims description 2
150000004792 aryl magnesium halides Chemical class 0.000 claims description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
229910052794 bromium Inorganic materials 0.000 claims description 2
125000004432 carbon atom Chemical group C* 0.000 claims description 2
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 2
QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 claims 2
238000005727 Friedel-Crafts reaction Methods 0.000 claims 2
239000012965 benzophenone Substances 0.000 claims 2
230000015572 biosynthetic process Effects 0.000 claims 2
HJIAMFHSAAEUKR-UHFFFAOYSA-N (2-hydroxyphenyl)-phenylmethanone Chemical group OC1=CC=CC=C1C(=O)C1=CC=CC=C1 HJIAMFHSAAEUKR-UHFFFAOYSA-N 0.000 claims 1
150000007513 acids Chemical class 0.000 claims 1
150000001491 aromatic compounds Chemical class 0.000 claims 1
RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 claims 1
150000008366 benzophenones Chemical class 0.000 claims 1
150000001875 compounds Chemical class 0.000 claims 1
238000006482 condensation reaction Methods 0.000 claims 1
150000001564 phenyl benzoates Chemical class 0.000 claims 1
238000006552 photochemical reaction Methods 0.000 claims 1
230000009257 reactivity Effects 0.000 claims 1
230000008707 rearrangement Effects 0.000 claims 1
238000003786 synthesis reaction Methods 0.000 claims 1
150000007964 xanthones Chemical class 0.000 claims 1
150000002825 nitriles Chemical class 0.000 abstract description 2
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 abstract 2
UIPBHEMSRLPBRL-UHFFFAOYSA-N 1-amino-3-(tert-butylamino)propan-2-ol Chemical compound CC(C)(C)NCC(O)CN UIPBHEMSRLPBRL-UHFFFAOYSA-N 0.000 abstract 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
125000004414 alkyl thio group Chemical group 0.000 abstract 1
239000011737 fluorine Substances 0.000 abstract 1
239000001294 propane Substances 0.000 abstract 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
238000010992 reflux Methods 0.000 description 7
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
238000003756 stirring Methods 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
MYMYVYZLMUEVED-UHFFFAOYSA-N 2-bromo-1,3-dimethylbenzene Chemical compound CC1=CC=CC(C)=C1Br MYMYVYZLMUEVED-UHFFFAOYSA-N 0.000 description 4
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
239000000155 melt Substances 0.000 description 4
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
KFZMGEQAYNKOFK-UHFFFAOYSA-N isopropyl alcohol Natural products CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
239000012071 phase Substances 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
239000000047 product Substances 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
IXHQHRPIXUFVGN-UHFFFAOYSA-N 1-phenyl-1-(2,3,4-trimethylphenyl)ethanol Chemical compound CC1=C(C(=C(C(C2=CC=CC=C2)(O)C)C=C1)C)C IXHQHRPIXUFVGN-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
125000001931 aliphatic group Chemical group 0.000 description 2
239000004305 biphenyl Substances 0.000 description 2
235000010290 biphenyl Nutrition 0.000 description 2
125000006267 biphenyl group Chemical group 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
238000001816 cooling Methods 0.000 description 2
239000013078 crystal Substances 0.000 description 2
150000004292 cyclic ethers Chemical class 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
239000000725 suspension Substances 0.000 description 2
125000003698 tetramethyl group Chemical group [H]C([H])([H])* 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
VVAKEQGKZNKUSU-UHFFFAOYSA-N 2,3-dimethylaniline Chemical group CC1=CC=CC(N)=C1C VVAKEQGKZNKUSU-UHFFFAOYSA-N 0.000 description 1
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
RAWZVIWEDAGMPW-UHFFFAOYSA-N 2-bromo-5-methoxy-1,3-dimethylbenzene Chemical compound COC1=CC(C)=C(Br)C(C)=C1 RAWZVIWEDAGMPW-UHFFFAOYSA-N 0.000 description 1
BJUWTPSGHDWTSW-UHFFFAOYSA-N 2-phenyl-2-(2,3,4,5-tetramethylphenyl)acetic acid Chemical group CC=1C(=C(C(=C(C=1)C(C(=O)O)C1=CC=CC=C1)C)C)C BJUWTPSGHDWTSW-UHFFFAOYSA-N 0.000 description 1
XFMUCDRJXZLSNE-UHFFFAOYSA-N 4-methoxy-2,6-dimethylaniline Chemical compound COC1=CC(C)=C(N)C(C)=C1 XFMUCDRJXZLSNE-UHFFFAOYSA-N 0.000 description 1
DLYMYMHRSCHIEG-UHFFFAOYSA-N 5-chloro-1,3,5-trimethylcyclohexa-1,3-diene Chemical group CC1=CC(C)=CC(C)(Cl)C1 DLYMYMHRSCHIEG-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
229910021589 Copper(I) bromide Inorganic materials 0.000 description 1
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
229910021607 Silver chloride Inorganic materials 0.000 description 1
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
PVQATPQSBYNMGE-UHFFFAOYSA-N [benzhydryloxy(phenyl)methyl]benzene Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)OC(C=1C=CC=CC=1)C1=CC=CC=C1 PVQATPQSBYNMGE-UHFFFAOYSA-N 0.000 description 1
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
230000021736 acetylation Effects 0.000 description 1
238000006640 acetylation reaction Methods 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
229940092714 benzenesulfonic acid Drugs 0.000 description 1
238000009835 boiling Methods 0.000 description 1
230000031709 bromination Effects 0.000 description 1
238000005893 bromination reaction Methods 0.000 description 1
WEDIIKBPDQQQJU-UHFFFAOYSA-N butane-1-sulfonyl chloride Chemical compound CCCCS(Cl)(=O)=O WEDIIKBPDQQQJU-UHFFFAOYSA-N 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000005660 chlorination reaction Methods 0.000 description 1
NKNDPYCGAZPOFS-UHFFFAOYSA-M copper(i) bromide Chemical compound Br[Cu] NKNDPYCGAZPOFS-UHFFFAOYSA-M 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
239000012954 diazonium Substances 0.000 description 1
150000001989 diazonium salts Chemical group 0.000 description 1
238000006193 diazotization reaction Methods 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000007789 gas Substances 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
239000002198 insoluble material Substances 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
239000011630 iodine Substances 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
PJYPCKZZTIAODG-UHFFFAOYSA-M magnesium;1,2-dimethylbenzene-6-ide;bromide Chemical compound [Mg+2].[Br-].CC1=CC=C[C-]=C1C PJYPCKZZTIAODG-UHFFFAOYSA-M 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
125000000466 oxiranyl group Chemical group 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
NQCBIMOYRRMVNA-UHFFFAOYSA-N propane-1,2,3-triol;hydrochloride Chemical compound Cl.OCC(O)CO NQCBIMOYRRMVNA-UHFFFAOYSA-N 0.000 description 1
238000000746 purification Methods 0.000 description 1
125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 description 1
HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 description 1
150000003462 sulfoxides Chemical class 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
238000007514 turning Methods 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000003643 water by type Substances 0.000 description 1
238000005303 weighing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/08—Preparation of carboxylic acids or their salts, halides or anhydrides from nitriles

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Oil, Petroleum & Natural Gas (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Steroid Compounds (AREA)

CH46777A 1976-01-14 1977-01-14 Process for the production of substituted benzhydrols CH618154A5 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
FR7600775A FR2338237A1 (fr)	1976-01-14	1976-01-14	Nouveau procede d'obtention de benzhydrols substitues

Publications (1)

Publication Number	Publication Date
CH618154A5 true CH618154A5 (en)	1980-07-15

Family

ID=9167884

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH46777A CH618154A5 (en)	1976-01-14	1977-01-14	Process for the production of substituted benzhydrols

Country Status (11)

Country	Link
JP (1)	JPS52116445A (2)
AR (1)	AR218239A1 (2)
CA (1)	CA1094107A (2)
CH (1)	CH618154A5 (2)
ES (1)	ES454932A1 (2)
FR (1)	FR2338237A1 (2)
IN (1)	IN143959B (2)
NL (1)	NL7700351A (2)
OA (1)	OA05539A (2)
PL (1)	PL195312A1 (2)
SU (1)	SU895281A3 (2)

1976
- 1976-01-14 FR FR7600775A patent/FR2338237A1/fr active Granted
- 1976-12-31 OA OA56041A patent/OA05539A/xx unknown
1977
- 1977-01-04 IN IN5/CAL/77A patent/IN143959B/en unknown
- 1977-01-11 CA CA270,264A patent/CA1094107A/fr not_active Expired
- 1977-01-11 ES ES454932A patent/ES454932A1/es not_active Expired
- 1977-01-12 AR AR266158A patent/AR218239A1/es active
- 1977-01-13 SU SU772439830A patent/SU895281A3/ru active
- 1977-01-14 PL PL19531277A patent/PL195312A1/xx unknown
- 1977-01-14 JP JP346877A patent/JPS52116445A/ja active Pending
- 1977-01-14 CH CH46777A patent/CH618154A5/fr not_active IP Right Cessation
- 1977-01-14 NL NL7700351A patent/NL7700351A/xx active Search and Examination

Also Published As

Publication number	Publication date
JPS52116445A (en)	1977-09-29
PL195312A1 (pl)	1978-02-27
FR2338237B1 (2)	1980-04-11
OA05539A (fr)	1981-04-30
FR2338237A1 (fr)	1977-08-12
SU895281A3 (ru)	1981-12-30
ES454932A1 (es)	1977-12-16
CA1094107A (fr)	1981-01-20
IN143959B (2)	1978-03-04
NL7700351A (nl)	1977-07-18
AR218239A1 (es)	1980-05-30

Legal Events

Date	Code	Title	Description
1981-09-30	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
CA1212380A (fr)	1986-10-07	Procede de preparation de nouveaux derives de thieno (2,3-b) pyrrole
FR2468590A1 (fr)	1981-05-08	Procede de preparation de 2,5-bis (2,2,2-trifluorethoxy)-n-(2-piperidylmethyl) benzamide a partir de 2,5-bis (2,2,2-trifluorethoxy)-a, a, a-trichloracetophenone
JP4272271B2 (ja)	2009-06-03	ハロゲノ−ｏ−ヒドロキシジフェニル化合物の製造方法
CH316025A (fr)	1956-09-15	Procédé de préparation de 3,5-diamino-6-aryl-1,2,4-triazines
JPH05246985A (ja)	1993-09-24	ビスマレインイミド誘導体の製造方法
CH618154A5 (en)	1980-07-15	Process for the production of substituted benzhydrols
CH630893A5 (fr)	1982-07-15	Procede de preparation d'o-(2,6-dichloroanilino)phenylacetamides n,n-disubstitues.
CH369442A (fr)	1963-05-31	Procédé de préparation de mono- et dicarbamates de 2,2-dichloro-1-aryl-1,3-prpane-diols
JP2002527417A (ja)	2002-08-27	化学的方法
CH392483A (fr)	1965-05-31	Procédé de préparation de nouveaux esters d'acides 4-halo-3-sulfamoyl-benzoïques
CA2064864A1 (fr)	1991-12-23	Procede de preparation de 1,1-bis(chlorophenyl)-2,2,2 trichloroethanol
FR2643900A1 (fr)	1990-09-07	Fonctionnalisation en position n + 1 de derives aryliques disubstitues en position n et n + 2
BE584061A (2)
CH623818A5 (en)	1981-06-30	Process for producing derivatives of thiochroman
JP2002097160A (ja)	2002-04-02	芳香族ヨウ素化物の製造法
JPH02295946A (ja)	1990-12-06	置換されたビフエニルカルボン酸およびその製法
BE817776Q (fr)	1975-01-17	Nouveaux derives de 5-phenyl-tetrazoles
BE481598A (2)
Hammond et al.	0	Synthesis and applications of S-(trifluoromethyl)-2, 8-bis (trifluoromethoxy) dibenzothiophenium triflate (Umemoto reagent IV)
CH618155A5 (2)	1980-07-15
EP0009487A1 (fr)	1980-04-16	Nouveaux derives de la benzamide.
CH487178A (fr)	1970-03-15	Procédé de préparation de dérivés de la phénothiazine
FR2553762A1 (fr)	1985-04-26	1,3-bis(3-aminophenoxy)-5-halogenobenzenes et leur procede de preparation
BE567029A (2)
BR112019002829B1 (pt)	2024-07-09	Método para preparação de derivados de 2,3-di-hidro-1-benzofurano substituído por ciclização de sais de etanol 2-(2-diazônio-6-fenil substituído)