CA1125784A - Process for manufacturing racemic parahydroxymandelic acid - Google Patents

Process for manufacturing racemic parahydroxymandelic acid

Info

Publication number: CA1125784A
Authority: CA; Canada
Prior art keywords: acid; glyoxylic acid; phenol; water; racemic
Prior art date: 1978-11-03
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

CA337,999A

Other languages

English (en)

French (fr)

Inventor

Alain Schouteeten

Yani Christidis

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.)

Sanofi Aventis France

Original Assignee

Francaise Hoechst Ste

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.)

1978-11-03

Filing date

1979-10-19

Publication date

1982-06-15

1979-10-19 Application filed by Francaise Hoechst Ste filed Critical Francaise Hoechst Ste

1982-06-15 Application granted granted Critical

1982-06-15 Publication of CA1125784A publication Critical patent/CA1125784A/en

Status Expired legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 25
YHXHKYRQLYQUIH-UHFFFAOYSA-N 4-hydroxymandelic acid Chemical compound OC(=O)C(O)C1=CC=C(O)C=C1 YHXHKYRQLYQUIH-UHFFFAOYSA-N 0.000 title claims abstract description 9
238000004519 manufacturing process Methods 0.000 title claims abstract description 6
HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical compound OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 claims abstract description 72
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 27
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 26
239000003795 chemical substances by application Substances 0.000 claims abstract description 5
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 28
238000009833 condensation Methods 0.000 claims description 13
230000005494 condensation Effects 0.000 claims description 13
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims 6
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 2
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
239000000243 solution Substances 0.000 description 12
239000012299 nitrogen atmosphere Substances 0.000 description 9
235000011121 sodium hydroxide Nutrition 0.000 description 8
LHGVFZTZFXWLCP-UHFFFAOYSA-N guaiacol Chemical compound COC1=CC=CC=C1O LHGVFZTZFXWLCP-UHFFFAOYSA-N 0.000 description 6
239000008188 pellet Substances 0.000 description 6
239000002253 acid Substances 0.000 description 5
-1 racemic parahydroxymandelic acid mono-hydrate Chemical class 0.000 description 5
238000003756 stirring Methods 0.000 description 5
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
239000012736 aqueous medium Substances 0.000 description 4
238000001704 evaporation Methods 0.000 description 4
230000008020 evaporation Effects 0.000 description 4
239000001117 sulphuric acid Substances 0.000 description 4
235000011149 sulphuric acid Nutrition 0.000 description 4
150000007513 acids Chemical class 0.000 description 3
239000008346 aqueous phase Substances 0.000 description 3
238000001816 cooling Methods 0.000 description 3
229960001867 guaiacol Drugs 0.000 description 3
230000007062 hydrolysis Effects 0.000 description 3
238000006460 hydrolysis reaction Methods 0.000 description 3
239000002904 solvent Substances 0.000 description 3
RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 description 2
238000005705 Cannizzaro reaction Methods 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
238000000605 extraction Methods 0.000 description 2
150000004682 monohydrates Chemical class 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
238000006722 reduction reaction Methods 0.000 description 2
238000010992 reflux Methods 0.000 description 2
HFFLGKNGCAIQMO-UHFFFAOYSA-N trichloroacetaldehyde Chemical compound ClC(Cl)(Cl)C=O HFFLGKNGCAIQMO-UHFFFAOYSA-N 0.000 description 2
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
RGHMISIYKIHAJW-UHFFFAOYSA-N 3,4-dihydroxymandelic acid Chemical compound OC(=O)C(O)C1=CC=C(O)C(O)=C1 RGHMISIYKIHAJW-UHFFFAOYSA-N 0.000 description 1
WSGYTJNNHPZFKR-UHFFFAOYSA-N 3-hydroxypropanenitrile Chemical compound OCCC#N WSGYTJNNHPZFKR-UHFFFAOYSA-N 0.000 description 1
AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical class OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 1
CGQCWMIAEPEHNQ-UHFFFAOYSA-N Vanillylmandelic acid Chemical compound COC1=CC(C(O)C(O)=O)=CC=C1O CGQCWMIAEPEHNQ-UHFFFAOYSA-N 0.000 description 1
150000001299 aldehydes Chemical class 0.000 description 1
239000012670 alkaline solution Substances 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
150000003934 aromatic aldehydes Chemical class 0.000 description 1
230000000911 decarboxylating effect Effects 0.000 description 1
230000001627 detrimental effect Effects 0.000 description 1
238000001035 drying Methods 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
238000009776 industrial production Methods 0.000 description 1
238000009434 installation Methods 0.000 description 1
238000011031 large-scale manufacturing process Methods 0.000 description 1
239000002609 medium Substances 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
MJGFBOZCAJSGQW-UHFFFAOYSA-N mercury sodium Chemical compound [Na].[Hg] MJGFBOZCAJSGQW-UHFFFAOYSA-N 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
230000003472 neutralizing effect Effects 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
238000004904 shortening Methods 0.000 description 1
229910001023 sodium amalgam Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/367—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by introduction of functional groups containing oxygen only in singly bound form

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Engineering & Computer Science (AREA)
Oil, Petroleum & Natural Gas (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

CA337,999A 1978-11-03 1979-10-19 Process for manufacturing racemic parahydroxymandelic acid Expired CA1125784A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
FR7831123A FR2440350A1 (fr)	1978-11-03	1978-11-03	Procede de fabrication de l'acide parahydroxymandelique racemique
FR7831123		1978-11-03

Publications (1)

Publication Number	Publication Date
CA1125784A true CA1125784A (en)	1982-06-15

Family

ID=9214433

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA337,999A Expired CA1125784A (en)	1978-11-03	1979-10-19	Process for manufacturing racemic parahydroxymandelic acid

Country Status (10)

Country	Link
JP (1)	JPS5564546A (it)
BE (1)	BE879359A (it)
CA (1)	CA1125784A (it)
CH (1)	CH642047A5 (it)
DE (1)	DE2944295C2 (it)
FR (1)	FR2440350A1 (it)
GB (1)	GB2034308B (it)
IE (1)	IE49308B1 (it)
IT (1)	IT1124842B (it)
NL (1)	NL189910C (it)

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2462415A1 (fr) *	1979-07-25	1981-02-13	Hoechst France	Procede de preparation d'acides hydroxyarylglycoliques racemiques et produits nouveaux en resultant
FR2495137A1 (fr) *	1980-11-28	1982-06-04	Hoechst France	Procede industriel de preparation en continu de l'acide p-hydroxymandelique racemique
US5252643A (en) *	1991-07-01	1993-10-12	Ciba-Geigy Corporation	Thiomethylated benzofuran-2-ones
TW206220B (it) *	1991-07-01	1993-05-21	Ciba Geigy Ag
EP0545861B1 (de) *	1991-11-29	1995-12-27	Ciba-Geigy Ag	Diphenylessigsäurederivate als Stabilisatoren für organisches Material
NL9300801A (nl) *	1992-05-22	1993-12-16	Ciba Geigy	3-(acyloxyfenyl)benzofuran-2-on als stabilisatoren.
TW260686B (it) *	1992-05-22	1995-10-21	Ciba Geigy
GB2267490B (en) *	1992-05-22	1995-08-09	Ciba Geigy Ag	3-(Carboxymethoxyphenyl)benzofuran-2-one stabilisers
MX9305489A (es) *	1992-09-23	1994-03-31	Ciba Geigy Ag	3-(dihidrobenzofuran-5-il)benzofuran-2-onas, estabilizadores.
TW255902B (it) *	1992-09-23	1995-09-01	Ciba Geigy
FR2705669B1 (fr) *	1993-05-28	1995-08-25	Hoechst France	Procédé de préparation d'acides hydroxyphénylacétiques.

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE617763C (de) *	1932-03-22	1935-08-24	J D Riedel E De Haeen Akt Ges	Verfahren zur Herstellung von aromatischen Oxyaldehyden
DE621567C (de) *	1932-06-25	1935-11-09	J D Riedel E De Haeen A G	Verfahren zur Herstellung von aromatischen Oxyaldehyden
DE2115551C3 (de) *	1971-03-31	1980-01-10	Haarmann & Reimer Gmbh, 3450 Holzminden	Verfahren zur Herstellung von aromatischen Hydroxyaldehyden

1978
- 1978-11-03 FR FR7831123A patent/FR2440350A1/fr active Granted
1979
- 1979-10-11 BE BE0/197604A patent/BE879359A/fr not_active IP Right Cessation
- 1979-10-18 CH CH938079A patent/CH642047A5/fr not_active IP Right Cessation
- 1979-10-19 CA CA337,999A patent/CA1125784A/en not_active Expired
- 1979-10-29 GB GB7937472A patent/GB2034308B/en not_active Expired
- 1979-10-29 JP JP13972579A patent/JPS5564546A/ja active Pending
- 1979-10-30 IT IT26924/79A patent/IT1124842B/it active
- 1979-11-02 DE DE2944295A patent/DE2944295C2/de not_active Expired
- 1979-11-02 IE IE2108/79A patent/IE49308B1/en not_active IP Right Cessation
- 1979-11-05 NL NLAANVRAGE7908100,A patent/NL189910C/xx not_active IP Right Cessation

Also Published As

Publication number	Publication date
CH642047A5 (fr)	1984-03-30
DE2944295C2 (de)	1982-02-04
IE792108L (en)	1980-05-03
GB2034308A (en)	1980-06-04
IE49308B1 (en)	1985-09-18
FR2440350A1 (fr)	1980-05-30
IT1124842B (it)	1986-05-14
FR2440350B1 (it)	1981-05-22
NL7908100A (nl)	1980-05-07
GB2034308B (en)	1983-03-30
BE879359A (fr)	1980-04-11
NL189910B (nl)	1993-04-01
NL189910C (nl)	1993-09-01
JPS5564546A (en)	1980-05-15
DE2944295A1 (de)	1980-05-08
IT7926924A0 (it)	1979-10-30

Legal Events

Date	Code	Title	Description
1999-06-15	MKEX	Expiry

Publication	Publication Date	Title
Thoer et al.	1988	The Reimer-Tiemann reaction in slightly hydrated solid-liquid medium: A new method for the synthesis of formyl and diformyl phenols
GB2034308A (en)	1980-06-04	Process for Manufacturing Racemic Parahydroxymandelic Acid
US3935257A (en)	1976-01-27	Chemical compounds
US4156093A (en)	1979-05-22	Process for increasing the production or recovery yields of hemiacetal-esters of glyoxylic acid
JPH051776B2 (it)	1993-01-11
US4259521A (en)	1981-03-31	Process for resolving DL-mandelic acid
JP3968158B2 (ja)	2007-08-29	ｏ− フタルアルデヒドの精製方法
US4408070A (en)	1983-10-04	Pure crystalline racemic sodium parahydroxymandelate, process for its preparation and uses thereof
WO2010119117A1 (en)	2010-10-21	Process for the preparation of 2,4,6-octatriene-1-oic acid and 2,4,6-octatriene-1-ol
US3878240A (en)	1975-04-15	Preparation of 2 alkoxy-5-alkylsulphonyl-benzoic acids
CA1153009A (en)	1983-08-30	Process for the preparation of 1,5-dimethylbicyclo(3.2.1)octanol-8
Reeve et al.	1975	Stereochemical study of the mechanism of the conversion of phenyl (trichloromethyl) carbinol to. alpha.-methoxyphenylacetic acid
CN115572272A (zh)	2023-01-06	非布司他及其醛基酯类中间体的制备方法
DK143332B (da)	1981-08-10	Fremgangsmaade til fremstilling af orthohydroxyalkylerede phenoler
FR2462415A1 (fr)	1981-02-13	Procede de preparation d'acides hydroxyarylglycoliques racemiques et produits nouveaux en resultant
US2304537A (en)	1942-12-08	Preparation of alpha-chlormethyl naphthalene
US4504678A (en)	1985-03-12	Pure crystalline racemic sodium parahydroxymandelate, process for its preparation and uses thereof
JPH02149586A (ja)	1990-06-08	メタ硼酸アリールの製造方法及びｏ―ヒドロキシベンジルアルコール類の製造へのメタ硼酸アリールの利用
US4260815A (en)	1981-04-07	Process for preparing a solution of DL-mandelic acid
US5302748A (en)	1994-04-12	Esterification process
US2768967A (en)	1956-10-30	Process for manufacture of 2, 5 diketo-8-nonen-3-ol
US2463734A (en)	1949-03-08	Racemization of optical isomers
Marvel et al.	1938	A CONVENIENT SYNTHESIS OF dl-GLUTAMIC ACID
SU379557A1 (ru)	1973-04-20	Способ получения 2,4-диалкил-2,4- -динитропентандиолов-1,5
US3024250A (en)	1962-03-06	Certificate of correction