JPS6128650B2 - - Google Patents

Info

Publication number: JPS6128650B2
Authority: JP; Japan
Prior art keywords: phenol; hydroxybenzyl; weight; hemiformal; hydroxybenzyl alcohol
Prior art date: 1982-10-07
Legal status (The legal status 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 status listed.): Expired

Application number

JP57175299A

Other languages

English (en)

Japanese (ja)

Other versions

JPS5965033A (ja

Inventor

Kyoshi Aonuma

Hiroyuki Oonuki

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

TAIMEI KK

Original Assignee

TAIMEI KK

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.)

1982-10-07

Filing date

1982-10-07

Publication date

1986-07-01

1982-10-07 Application filed by TAIMEI KK filed Critical TAIMEI KK

1982-10-07 Priority to JP57175299A priority Critical patent/JPS5965033A/ja

1984-04-13 Publication of JPS5965033A publication Critical patent/JPS5965033A/ja

1986-07-01 Publication of JPS6128650B2 publication Critical patent/JPS6128650B2/ja

Status Granted legal-status Critical Current

Links

ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 91
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 28
150000005846 sugar alcohols Polymers 0.000 claims description 27
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 26
-1 hydroxybenzyl alcohols Chemical class 0.000 claims description 25
238000000034 method Methods 0.000 claims description 24
239000003054 catalyst Substances 0.000 claims description 22
150000001875 compounds Chemical class 0.000 claims description 22
238000004519 manufacturing process Methods 0.000 claims description 21
125000003118 aryl group Chemical group 0.000 claims description 20
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 18
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 15
125000004432 carbon atom Chemical group C* 0.000 claims description 7
150000007514 bases Chemical class 0.000 claims description 6
KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims description 6
239000004327 boric acid Substances 0.000 claims description 6
229910052751 metal Inorganic materials 0.000 claims description 4
239000002184 metal Substances 0.000 claims description 4
150000003839 salts Chemical class 0.000 claims description 4
150000007524 organic acids Chemical class 0.000 claims description 3
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 90
CQRYARSYNCAZFO-UHFFFAOYSA-N salicyl alcohol Chemical compound OCC1=CC=CC=C1O CQRYARSYNCAZFO-UHFFFAOYSA-N 0.000 description 63
BVJSUAQZOZWCKN-UHFFFAOYSA-N p-hydroxybenzyl alcohol Chemical compound OCC1=CC=C(O)C=C1 BVJSUAQZOZWCKN-UHFFFAOYSA-N 0.000 description 57
238000006243 chemical reaction Methods 0.000 description 45
239000007788 liquid Substances 0.000 description 26
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 21
229930040373 Paraformaldehyde Natural products 0.000 description 14
229920002866 paraformaldehyde Polymers 0.000 description 14
239000000203 mixture Substances 0.000 description 13
238000002360 preparation method Methods 0.000 description 13
NXXYKOUNUYWIHA-UHFFFAOYSA-N 2,6-Dimethylphenol Chemical compound CC1=CC=CC(C)=C1O NXXYKOUNUYWIHA-UHFFFAOYSA-N 0.000 description 12
238000004458 analytical method Methods 0.000 description 11
238000003756 stirring Methods 0.000 description 11
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 8
ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 description 7
239000004246 zinc acetate Substances 0.000 description 7
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
239000002994 raw material Substances 0.000 description 6
230000000052 comparative effect Effects 0.000 description 5
238000010438 heat treatment Methods 0.000 description 5
HNURKXXMYARGAY-UHFFFAOYSA-N 2,6-Di-tert-butyl-4-hydroxymethylphenol Chemical compound CC(C)(C)C1=CC(CO)=CC(C(C)(C)C)=C1O HNURKXXMYARGAY-UHFFFAOYSA-N 0.000 description 4
RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
235000011187 glycerol Nutrition 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
QQOMQLYQAXGHSU-UHFFFAOYSA-N 236TMPh Natural products CC1=CC=C(C)C(O)=C1C QQOMQLYQAXGHSU-UHFFFAOYSA-N 0.000 description 3
ZVXBWEIAIZEPGR-UHFFFAOYSA-N 4-(hydroxymethyl)-2,6-dimethylphenol Chemical compound CC1=CC(CO)=CC(C)=C1O ZVXBWEIAIZEPGR-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
239000006227 byproduct Substances 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical class OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 description 3
OGRAOKJKVGDSFR-UHFFFAOYSA-N 2,3,5-trimethylphenol Chemical compound CC1=CC(C)=C(C)C(O)=C1 OGRAOKJKVGDSFR-UHFFFAOYSA-N 0.000 description 2
DECTVMOFPJKFOZ-UHFFFAOYSA-N 2,6-bis(hydroxymethyl)phenol Chemical compound OCC1=CC=CC(CO)=C1O DECTVMOFPJKFOZ-UHFFFAOYSA-N 0.000 description 2
DKCPKDPYUFEZCP-UHFFFAOYSA-N 2,6-di-tert-butylphenol Chemical compound CC(C)(C)C1=CC=CC(C(C)(C)C)=C1O DKCPKDPYUFEZCP-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
150000008044 alkali metal hydroxides Chemical class 0.000 description 2
239000003963 antioxidant agent Substances 0.000 description 2
PVAONLSZTBKFKM-UHFFFAOYSA-N diphenylmethanediol Chemical compound C=1C=CC=CC=1C(O)(O)C1=CC=CC=C1 PVAONLSZTBKFKM-UHFFFAOYSA-N 0.000 description 2
238000004821 distillation Methods 0.000 description 2
230000000694 effects Effects 0.000 description 2
FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 2
238000002156 mixing Methods 0.000 description 2
150000002989 phenols Chemical class 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 description 1
YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
ITWBWJFEJCHKSN-UHFFFAOYSA-N 1,4,7-triazonane Chemical compound C1CNCCNCCN1 ITWBWJFEJCHKSN-UHFFFAOYSA-N 0.000 description 1
HOPGWDUYWPMYFB-UHFFFAOYSA-N 2,4-bis(hydroxymethyl)phenol Chemical compound OCC1=CC=C(O)C(CO)=C1 HOPGWDUYWPMYFB-UHFFFAOYSA-N 0.000 description 1
UHOPWFKONJYLCF-UHFFFAOYSA-N 2-(2-sulfanylethyl)isoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(CCS)C(=O)C2=C1 UHOPWFKONJYLCF-UHFFFAOYSA-N 0.000 description 1
125000006290 2-hydroxybenzyl group Chemical group [H]OC1=C(C([H])=C([H])C([H])=C1[H])C([H])([H])* 0.000 description 1
WJQOZHYUIDYNHM-UHFFFAOYSA-N 2-tert-Butylphenol Chemical compound CC(C)(C)C1=CC=CC=C1O WJQOZHYUIDYNHM-UHFFFAOYSA-N 0.000 description 1
GOLORTLGFDVFDW-UHFFFAOYSA-N 3-(1h-benzimidazol-2-yl)-7-(diethylamino)chromen-2-one Chemical compound C1=CC=C2NC(C3=CC4=CC=C(C=C4OC3=O)N(CC)CC)=NC2=C1 GOLORTLGFDVFDW-UHFFFAOYSA-N 0.000 description 1
KPRWCZKBOOSXCP-UHFFFAOYSA-N 3-benzyl-2-hydroxybenzaldehyde Chemical compound C1=CC=C(C=O)C(O)=C1CC1=CC=CC=C1 KPRWCZKBOOSXCP-UHFFFAOYSA-N 0.000 description 1
QHPQWRBYOIRBIT-UHFFFAOYSA-N 4-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C=C1 QHPQWRBYOIRBIT-UHFFFAOYSA-N 0.000 description 1
DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
FIPWRIJSWJWJAI-UHFFFAOYSA-N Butyl carbitol 6-propylpiperonyl ether Chemical compound C1=C(CCC)C(COCCOCCOCCCC)=CC2=C1OCO2 FIPWRIJSWJWJAI-UHFFFAOYSA-N 0.000 description 1
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
RJUFJBKOKNCXHH-UHFFFAOYSA-N Methyl propionate Chemical compound CCC(=O)OC RJUFJBKOKNCXHH-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
229930182555 Penicillin Natural products 0.000 description 1
JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
239000002253 acid Substances 0.000 description 1
239000003905 agrochemical Substances 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
239000003242 anti bacterial agent Substances 0.000 description 1
229940088710 antibiotic agent Drugs 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
229940043232 butyl acetate Drugs 0.000 description 1
LHQLJMJLROMYRN-UHFFFAOYSA-L cadmium acetate Chemical compound [Cd+2].CC([O-])=O.CC([O-])=O LHQLJMJLROMYRN-UHFFFAOYSA-L 0.000 description 1
BAAYWLNVHTVAJJ-UHFFFAOYSA-L cadmium(2+);diformate Chemical compound [Cd+2].[O-]C=O.[O-]C=O BAAYWLNVHTVAJJ-UHFFFAOYSA-L 0.000 description 1
239000000470 constituent Substances 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
150000001896 cresols Chemical class 0.000 description 1
235000014113 dietary fatty acids Nutrition 0.000 description 1
239000003814 drug Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
229940093499 ethyl acetate Drugs 0.000 description 1
PFCHFHIRKBAQGU-UHFFFAOYSA-N ethyl n-propyl ketone Natural products CCCC(=O)CC PFCHFHIRKBAQGU-UHFFFAOYSA-N 0.000 description 1
229930195729 fatty acid Natural products 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
239000012456 homogeneous solution Substances 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
239000002917 insecticide Substances 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
229940017219 methyl propionate Drugs 0.000 description 1
239000003607 modifier Substances 0.000 description 1
DWFKOMDBEKIATP-UHFFFAOYSA-N n'-[2-[2-(dimethylamino)ethyl-methylamino]ethyl]-n,n,n'-trimethylethane-1,2-diamine Chemical compound CN(C)CCN(C)CCN(C)CCN(C)C DWFKOMDBEKIATP-UHFFFAOYSA-N 0.000 description 1
YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
229940049954 penicillin Drugs 0.000 description 1
WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
UKODFQOELJFMII-UHFFFAOYSA-N pentamethyldiethylenetriamine Chemical compound CN(C)CCN(C)CCN(C)C UKODFQOELJFMII-UHFFFAOYSA-N 0.000 description 1
XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 1
239000002304 perfume Substances 0.000 description 1
239000012450 pharmaceutical intermediate Substances 0.000 description 1
229960005235 piperonyl butoxide Drugs 0.000 description 1
239000005648 plant growth regulator Substances 0.000 description 1
229920000768 polyamine Polymers 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
229940090181 propyl acetate Drugs 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000010409 thin film Substances 0.000 description 1
NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
238000005406 washing Methods 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
239000008096 xylene Substances 0.000 description 1
150000003739 xylenols Chemical class 0.000 description 1
SRWMQSFFRFWREA-UHFFFAOYSA-M zinc formate Chemical compound [Zn+2].[O-]C=O SRWMQSFFRFWREA-UHFFFAOYSA-M 0.000 description 1

Classifications

- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts

Landscapes

Catalysts (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

JP57175299A 1982-10-07 1982-10-07 ヒドロキシベンジルアルコ−ル類の製造方法 Granted JPS5965033A (ja)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP57175299A JPS5965033A (ja)	1982-10-07	1982-10-07	ヒドロキシベンジルアルコ−ル類の製造方法

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP57175299A JPS5965033A (ja)	1982-10-07	1982-10-07	ヒドロキシベンジルアルコ−ル類の製造方法

Publications (2)

Publication Number	Publication Date
JPS5965033A JPS5965033A (ja)	1984-04-13
JPS6128650B2 true JPS6128650B2 (fr)	1986-07-01

Family

ID=15993666

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP57175299A Granted JPS5965033A (ja)	1982-10-07	1982-10-07	ヒドロキシベンジルアルコ−ル類の製造方法

Country Status (1)

Country	Link
JP (1)	JPS5965033A (fr)

1982
- 1982-10-07 JP JP57175299A patent/JPS5965033A/ja active Granted

Also Published As

Publication number	Publication date
JPS5965033A (ja)	1984-04-13

Publication	Publication Date	Title
Christensen	1975	Preparation of salicylaldehydes via the ortho-lithio derivatives of methoxymethyl-protected phenols
EP0466319B1 (fr)	1998-05-06	Hydroxyalcoylation de phénols ou de thiophénols au moyen de carbonates organiques cycliques utilisant des catalyseurs triorganophosphines
US3855306A (en)	1974-12-17	Process for the preparation of 2,4,5-trimethoxybenzaldehyde
US6465697B1 (en)	2002-10-15	Catalyst promotor for the manufacture of polyphenols
US4201878A (en)	1980-05-06	Process for producing bisphenols
US2885385A (en)	1959-05-05	Polyphenylol derivatives of olefinic aldehydes
JPS6128650B2 (fr)	1986-07-01
US4663478A (en)	1987-05-05	Process for producing a para-substituted phenol derivative
US3819719A (en)	1974-06-25	Production of alkoxy phenolic compounds
EP0065289B1 (fr)	1985-01-23	Procédé de synthèse du trialcoyl-tris (3,5-dialcoyl-4-hydroxybenzyl)-benzène
JP3882486B2 (ja)	2007-02-14	オキセタン環を有するエーテル化合物の製造方法
US3992452A (en)	1976-11-16	Method for the production of alkoxycyclohexanones
US4163116A (en)	1979-07-31	Process for producing bisphenols
US4324922A (en)	1982-04-13	Reimer-Tiemann aldehyde synthesis process
EP0001910A1 (fr)	1979-05-16	Préparation de dihydroxy-4,4' stilbènes ou de leurs dérivés
USRE29200E (en)	1977-05-03	Production of alkoxy phenolic compounds
US4108909A (en)	1978-08-22	N-alkylated cresylic acids via direct alkylation in a liquid phase
USRE29201E (en)	1977-05-03	Production of alkoxy phenolic compounds
JP2688437B2 (ja)	1997-12-10	ヒドロキシメチル―ジハロ―ジアルキルフェノールの合成法
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