Methyl Thioglycolate → Methyl [[bis-(2-chlorophenyl)methyl]thio]acetate

HRID 1898948

Reaction equation

HRID 1898948 reaction equation
[Cl:1][C:2]1[CH:16]=[CH:15][CH:14]=[CH:13][C:3]=1[CH:4](O)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[Cl:11].[C:17]([O:21][CH3:22])(=[O:20])[CH2:18][SH:19]>>[Cl:1][C:2]1[CH:16]=[CH:15][CH:14]=[CH:13][C:3]=1[CH:4]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[Cl:11])[S:19][CH2:18][C:17]([O:21][CH3:22])=[O:20]

Participants

3

Reactant 2

HCID 16907Methyl ThioglycolateHCID 230561Bis(2-chlorophenyl)methanol

Product 1

HCID 53974093Methyl [[bis-(2-chlorophenyl)methyl]thio]acetateYield 23%

Procedure

Following the procedure of Example 4, 2,2'-dichlorobenzhydrol, synthesized in accordance with C. W. N. Cumper, et. al. in J. C. S. Perkins Trans. II (1), 106 (1972)] is reacted with methyl thioglycolate for 4 hours at 50°-60° C. Chromatography on silica gel, eluting with a gradient of 5% ethyl acetate in hexane to 10% ethyl acetate in hexane, gives methyl [[bis-(2-chlorophenyl)methyl]thio]acetate as a white solid in 23% yield: melting point 90°-92° C.

Workup

  1. customsynthesized in accordance with C
  2. washChromatography on silica gel, eluting with a gradient of 5% ethyl acetate in hexane to 10% ethyl acetate in hexane

Sources & evidence

ORD record
ord-6710bb53db9e451daa4dd891fedd33ff
Source dataset
uspto-grants-1996_11
Patent number
US05571825

Linked notes

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