Methyl Thioglycolate → Methyl [[bis-(4-methoxyphenyl)methyl]thio]acetate

HRID 1898943Notes

Reaction equation

HRID 1898943 reaction equation
[CH3:1][O:2][C:3]1[CH:18]=[CH:17][C:6]([CH:7](O)[C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=2)=[CH:5][CH:4]=1.[C:19]([O:23][CH3:24])(=[O:22])[CH2:20][SH:21]>Cl.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:18]=[CH:17][C:6]([CH:7]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=2)[S:21][CH2:20][C:19]([O:23][CH3:24])=[O:22])=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 16907Methyl ThioglycolateHCID 69768p,p'-Dimethoxybenzhydryl alcohol

Product 1

HCID 54478038Methyl [[bis-(4-methoxyphenyl)methyl]thio]acetateYield 73%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4,4'-dimethoxybenzhydrol (Aldrich) (300 mg, 1.23 mmol) and methyl thioglycolate (123 mg, 1.35 mmol) in 6 mL of 10% methanolic HCl is heated at reflux for 45 minutes. The reaction is cooled to room temperature, diluted with ethyl acetate, washed with saturated aqueous sodium bicarbonate, brine and dried over magnesium sulfate. The product is concentrated in vacuo to give methyl [[bis-(4-methoxyphenyl)methyl]thio]acetate as a colorless oil in 73% yield.

Workup

  1. temperatureat reflux for 45 minutes
  2. washwashed with saturated aqueous sodium bicarbonate, brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationThe product is concentrated in vacuo

Sources & evidence

ORD record
ord-5669fb0c689e4395bf147128b1a3ad91
Source dataset
uspto-grants-1996_11
Patent number
US05571825

Reaction notes

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