p-Chlorothiophenol → Methyl alpha-(p-chlorophenylthio)-alpha-[p-(p-chlorophenoxy)phenyl]acetate

HRID 1863277Notes

Reaction equation

HRID 1863277 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].[Cl:21][C:22]1[CH:27]=[CH:26][C:25]([SH:28])=[CH:24][CH:23]=1>CO>[Cl:21][C:22]1[CH:27]=[CH:26][C:25]([S:28][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:24][CH:23]=1

Participants

4

Reactant 2

HCID 7815p-ChlorothiophenolHCID 20392594Methyl alpha-Bromo-alpha-[p-(p-chlorophenoxy)phenyl]acetate

Product 1

HCID 20392626Methyl alpha-(p-chlorophenylthio)-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 3.61 g of 4-chlorothiophenol in methanol, as in Example 16, to give a yellow oil which is bulb distilled at 0.01 mm to afford a colorless oil (188° C.) which solidifies to give white crystals, mp 71°-75° C. A portion is recrystallized from hexane to give white needles, mp 74°-75.5° C.

Workup

  1. customto give a yellow oil which
  2. distillationdistilled at 0.01 mm
  3. customto afford a colorless oil (188° C.) which
  4. customto give white crystals, mp 71°-75° C
  5. customA portion is recrystallized from hexane
  6. customto give white needles, mp 74°-75.5° C.

Sources & evidence

ORD record
ord-5b08abcdb10949c8a9965a99733ae99e
Source dataset
uspto-grants-1979_09
Patent number
US04168385

Reaction notes

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