Benzene → Methyl [p-(p-chlorophenylthio)phenyl]acetate
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][C:16]([OH:18])=[O:17])=[CH:11][CH:10]=2)=[CH:4][CH:3]=1.S(Cl)(Cl)=O.[CH:23]1C=CC=CC=1>>[CH3:23][O:17][C:16](=[O:18])[CH2:15][C:12]1[CH:13]=[CH:14][C:9]([S:8][C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)=[CH:10][CH:11]=1Participants
4
Procedure
A mixture of 21 g of [p-(p-chlorophenylthio)phenyl]acetic acid and 11.9 g of thionyl chloride are stirred overnight at room temperature. To the resulting greenish yellow solution is added 20 ml of benzene and the solvent is evaporated at reduced pressure. This procedure is repeated once. The residue is added dropwise to 300 ml of methanol, maintained at 0° C., and the resulting solution is stirred overnight. The solvent is evaporated at reduced pressure and the mixture is dissolved in 200 ml of ether. The ether layer is washed with 100 ml of water, 100 ml of saturated NaHCO3, 100 ml of saturated brine and dried over MgSO4. Evaporation of the solvent and distillation of the residue affords the product as a light yellow oil.
Workup
- customthe solvent is evaporated at reduced pressure
- additionThe residue is added dropwise to 300 ml of methanol
- temperaturemaintained at 0° C.
- stirringthe resulting solution is stirred overnight
- customThe solvent is evaporated at reduced pressure
- dissolutionthe mixture is dissolved in 200 ml of ether
- washThe ether layer is washed with 100 ml of water, 100 ml of saturated NaHCO3, 100 ml of saturated brine
- dry with materialdried over MgSO4
- customEvaporation of the solvent and distillation of the residue
Sources & evidence
- ORD record
- ord-cf52bf2103934e9c953e785de26ac303
- Source dataset
- uspto-grants-1979_09
- Patent number
- US04168385
Reaction notes
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