Sulfuric Acid → (Phenylthio)acetic acid, cyclohexyl ester

HRID 477322

Reaction equation

HRID 477322 reaction equation
C(OCC)(=O)CCC[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[C:15]1([S:21][CH2:22][C:23]([OH:25])=[O:24])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.S(=O)(=O)(O)O>C1(O)CCCCC1>[C:15]1([S:21][CH2:22][C:23]([O:25][CH:5]2[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]2)=[O:24])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 8048Ethyl caprateHCID 59541(Phenylthio)acetic acid

Product 1

HCID 533051(Phenylthio)acetic acid, cyclohexyl ester

Reagents, catalysts & solvents 1

HCID 7966CyclohexanolSolvent

Procedure

The procedure is as in Example 20 for the preparation of ethyl n-decanoate, starting with (phenylthio)acetic acid (20 g) and 36N aqueous sulphuric acid solution (0.32 cc) in cyclohexanol (100 cc). After purification by chromatography on a silica column with a mixture of cyclohexane and ethyl acetate (70:30 by volume) as eluent, cyclohexyl (phenylthio)acetate (29 g) is obtained, and is used in the crude state in the subsequent phases.

Workup

  1. customAfter purification by chromatography on a silica column
  2. additionwith a mixture of cyclohexane and ethyl acetate (70:30 by volume) as eluent

Sources & evidence

ORD record
ord-b812ea055ace49c3bebc1247d743c93e
Source dataset
uspto-grants-1989_12
Patent number
US04886835

Linked notes

Loading…