Ethanethiol → 3-[(4-Hydroxyphenyl)methyl]glutaric acid

HRID 27371

Reaction equation

HRID 27371 reaction equation
C(S)C.C[O:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH:13]([CH2:18][C:19]([OH:21])=[O:20])[CH2:14][C:15]([OH:17])=[O:16])=[CH:8][CH:7]=1>CN(C)C=O>[OH:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH:13]([CH2:18][C:19]([OH:21])=[O:20])[CH2:14][C:15]([OH:17])=[O:16])=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 6343EthanethiolHCID 205288313-[(4-Methoxyphenyl)methyl]glutaric acid

Product 1

HCID 205288373-[(4-Hydroxyphenyl)methyl]glutaric acidYield 79.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Conditions

Temperature
165 °C

Procedure

To a stirred suspension of 57% sodium hydride-paraffin (1.4 g) in dry dimethylformamide (30 ml) is added dropwise a solution of ethanethiol (4.0 ml) in dry dimethylformamide (10 ml). After 15 minutes, a solution of 3-[(4-methoxyphenyl)methyl]glutaric acid (800 mg) in dry dimethylformamide (20 ml) is added. The resulting slurry is heated in a bath at 165° C. for 20 hours and evaporated in vacuo. The residue is acidified with 20% hydrochloric acid, extracted with ether and the extracts are discarded. The aqueous solution is saturated with salt and extracted with ethyl acetate. The extracts are combined, washed once with brine, dried, evaporated and the residue crystallized from a mixture of ethyl acetate-chloroform-hexane to give 600 mg of 3-[(4-hydroxyphenyl)methyl]glutaric acid, melting point 117°-119° C.

Workup

  1. customevaporated in vacuo
  2. extractionextracted with ether
  3. extractionextracted with ethyl acetate
  4. washwashed once with brine
  5. customdried
  6. customevaporated
  7. customthe residue crystallized from a mixture of ethyl acetate-chloroform-hexane

Sources & evidence

ORD record
ord-033aa82002814349b96762619854d38d
Source dataset
uspto-grants-1980_09
Patent number
US04221725

Linked notes

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