Thiophenol → Methyl alpha-(phenylthio)-alpha-[p-(p-chlorophenoxy)phenyl]acetate

HRID 1704024Notes

Reaction equation

HRID 1704024 reaction equation
Br[CH:2]([C:7]1[CH:12]=[CH:11][C:10]([O:13][C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)=[CH:9][CH:8]=1)[C:3]([O:5][CH3:6])=[O:4].[C:21]1([SH:27])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>CO>[C:21]1([S:27][CH:2]([C:7]2[CH:12]=[CH:11][C:10]([O:13][C:14]3[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=3)=[CH:9][CH:8]=2)[C:3]([O:5][CH3:6])=[O:4])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 7969ThiophenolHCID 20392594Methyl alpha-Bromo-alpha-[p-(p-chlorophenoxy)phenyl]acetate

Product 1

HCID 20392614Methyl alpha-(phenylthio)-alpha-[p-(p-chlorophenoxy)phenyl]acetate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl α-bromo-α-[p-(p-chlorophenoxy)phenyl]acetate (7.11 g) is reacted with 2.75 g of thiophenol in methanol, as in Example 16, to yield a yellow oil. After a brief distillation at 0.02 mm to remove volatile impurities, the residue is evaporatively distilled (173° C at 0.01 mm) to afford the product as a colorless oil which solidifies, mp 64°-68.5° C. A portion is recrystallized from hexane to give white plates, mp 71.5°-72.5° C.

Workup

  1. customto yield a yellow oil
  2. distillationAfter a brief distillation at 0.02 mm
  3. customto remove volatile impurities
  4. distillationthe residue is evaporatively distilled (173° C at 0.01 mm)

Sources & evidence

ORD record
ord-10e17b1ebd094993a082acc73828984f
Source dataset
uspto-grants-1978_11
Patent number
US04125729

Reaction notes

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