Ethanethiol → HCID 20528836, compound

HRID 1389043Notes

Reaction equation

HRID 1389043 reaction equation
C(S)C.C[O:5][C:6]1[CH:11]=[CH:10][C:9]([CH:12]([CH2:17][C:18]([OH:20])=[O:19])[CH2:13][C:14]([OH:16])=[O:15])=[CH:8][CH:7]=1>CN(C)C=O>[OH:5][C:6]1[CH:11]=[CH:10][C:9]([CH:12]([CH2:17][C:18]([OH:20])=[O:19])[CH2:13][C:14]([OH:16])=[O:15])=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 6343EthanethiolHCID 3472533-(4-Methoxyphenyl)pentanedioic acid

Product 1

HCID 20528836HCID 20528836, compoundYield 81.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Conditions

Temperature
165 °C

Procedure

To a stirred suspension of 57% sodium hydride-paraffin (6.45 g), in dry dimethylformamide (70 ml) is slowly added ethanethiol (11.89 ml) in dry dimethylformamide (20 ml). After stirring the resultant slurry for 15 minutes, a solution of 3-(4-methoxyphenyl)glutaric acid (3.0 g) in dry dimethylformamide (20 ml) is added. The slurry is heated in a bath at 165° C. for 5.0 hours and most of the solvent is removed by distillation in vacuo. The residue is diluted with water, acidified with concentrated hydrochloric acid and extracted twice with ether (the extracts are discarded). The solution is saturated with sodium chloride and extracted with ethyl acetate. The ethyl acetate solution is washed once with brine, dried and the residue cyrstallized from chloroform-hexane to afford 2.3 g of 3-(4-hydroxyphenyl)glutaric acid, melting point 168°-170° C.

Workup

  1. customis removed by distillation in vacuo
  2. additionThe residue is diluted with water
  3. extractionextracted twice with ether (the extracts
  4. extractionextracted with ethyl acetate
  5. washThe ethyl acetate solution is washed once with brine
  6. customdried

Sources & evidence

ORD record
ord-72d2dddcd98646cba4f1e9e078dada8a
Source dataset
uspto-grants-1981_01
Patent number
US04243608

Reaction notes

Loading…