Thioglycolic Acid → [[Bis(4-chlorophenyl)methyl]sulfanyl]acetic acid

HRID 1898944Notes

Reaction equation

HRID 1898944 reaction equation
[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([CH:6](O)[C:7]2[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.[SH:17][CH2:18][C:19]([OH:21])=[O:20].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1.C(OCC)(=O)C>[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([CH:6]([C:7]2[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=2)[S:17][CH2:18][C:19]([OH:21])=[O:20])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 1133Thioglycolic AcidHCID 70334,4'-DichlorobenzhydrolHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 22049849[[Bis(4-chlorophenyl)methyl]sulfanyl]acetic acid

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4,4'-dichlorobenzhydrol (Aldrich) (500 mg, 1.97 mmol), mercaptoacetic acid (181 mg, 1.97 mmol) and ρ-toluenesulfonic acid monohydrate (93 mg, 0.49 mmol) in 7 mL of toluene is stirred at room temperature for 2 hours followed by heating at 50°-60° C. for 1 hour. Upon cooling, the mixture is diluted with ethyl acetate, washed with water, brine, and dried over magnesium sulfate. The product is concentrated in vacuo to give [[bis-(4-chlorophenyl)methyl]thio]acetic acid as a pale yellow oil.

Workup

  1. temperatureby heating at 50°-60° C. for 1 hour
  2. temperatureUpon cooling
  3. washwashed with water, brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationThe product is concentrated in vacuo

Sources & evidence

ORD record
ord-30fd530eef214b28b7f013c15c775c07
Source dataset
uspto-grants-1996_11
Patent number
US05571825

Reaction notes

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