CA1125784A - Process for manufacturing racemic parahydroxymandelic acid - Google Patents
Process for manufacturing racemic parahydroxymandelic acidInfo
- Publication number
- CA1125784A CA1125784A CA337,999A CA337999A CA1125784A CA 1125784 A CA1125784 A CA 1125784A CA 337999 A CA337999 A CA 337999A CA 1125784 A CA1125784 A CA 1125784A
- Authority
- CA
- Canada
- Prior art keywords
- acid
- glyoxylic acid
- phenol
- water
- racemic
- Prior art date
- 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
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)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7831123 | 1978-11-03 | ||
| FR7831123A FR2440350A1 (fr) | 1978-11-03 | 1978-11-03 | Procede de fabrication de l'acide parahydroxymandelique racemique |
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 (de) |
| BE (1) | BE879359A (de) |
| CA (1) | CA1125784A (de) |
| CH (1) | CH642047A5 (de) |
| DE (1) | DE2944295C2 (de) |
| FR (1) | FR2440350A1 (de) |
| GB (1) | GB2034308B (de) |
| IE (1) | IE49308B1 (de) |
| IT (1) | IT1124842B (de) |
| NL (1) | NL189910C (de) |
Families Citing this family (11)
| 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 (de) * | 1991-07-01 | 1993-05-21 | Ciba Geigy Ag | |
| DE59204845D1 (de) * | 1991-11-29 | 1996-02-08 | 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 (de) * | 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 |
| TW255902B (de) * | 1992-09-23 | 1995-09-01 | Ciba Geigy | |
| MX9305489A (es) * | 1992-09-23 | 1994-03-31 | Ciba Geigy Ag | 3-(dihidrobenzofuran-5-il)benzofuran-2-onas, estabilizadores. |
| FR2705669B1 (fr) * | 1993-05-28 | 1995-08-25 | Hoechst France | Procédé de préparation d'acides hydroxyphénylacétiques. |
Family Cites Families (3)
| 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 JP JP13972579A patent/JPS5564546A/ja active Pending
- 1979-10-29 GB GB7937472A patent/GB2034308B/en not_active Expired
- 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 |
|---|---|
| GB2034308A (en) | 1980-06-04 |
| FR2440350B1 (de) | 1981-05-22 |
| IT1124842B (it) | 1986-05-14 |
| CH642047A5 (fr) | 1984-03-30 |
| DE2944295C2 (de) | 1982-02-04 |
| NL189910C (nl) | 1993-09-01 |
| FR2440350A1 (fr) | 1980-05-30 |
| GB2034308B (en) | 1983-03-30 |
| IE792108L (en) | 1980-05-03 |
| NL7908100A (nl) | 1980-05-07 |
| IE49308B1 (en) | 1985-09-18 |
| DE2944295A1 (de) | 1980-05-08 |
| IT7926924A0 (it) | 1979-10-30 |
| JPS5564546A (en) | 1980-05-15 |
| BE879359A (fr) | 1980-04-11 |
| NL189910B (nl) | 1993-04-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |