Benzoic acid, 2-mercapto-, methyl ester → Methyl 2-[(2,2-dimethoxy-1-phenylethyl)thio]benzoate

HRID 863448Notes

Reaction equation

HRID 863448 reaction equation
[SH:1][C:2]1[CH:11]=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].Br[CH:13]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH:14]([O:17][CH3:18])[O:15][CH3:16].C[O-].[Na+]>CO>[CH3:18][O:17][CH:14]([O:15][CH3:16])[CH:13]([S:1][C:2]1[CH:11]=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5])[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

5

Reactant 3

HCID 21009Benzoic acid, 2-mercapto-, methyl esterHCID 10942334Sodium MethoxideHCID 11064658(1-Bromo-2,2-dimethoxyethyl)benzene

Product 1

HCID 19696486Methyl 2-[(2,2-dimethoxy-1-phenylethyl)thio]benzoateYield 70%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In each case 10 ml of methyl 2-mercaptobenzoate and 2-bromo-1,1-dimethoxy-2-phenylethane are refluxed overnight in 30 ml of methanol, with addition of 10 ml of NaOMe. After working up and purification by chromatography, 70% of viscous oil is obtained.

Workup

  1. custompurification by chromatography

Sources & evidence

ORD record
ord-45b10d4831e14fa7b388c364bec5fa8f
Source dataset
uspto-grants-1998_02
Patent number
US05721248

Reaction notes

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