Water → Benzoic acid, 2-[[(4-methoxyphenyl)methyl]thio]-

HRID 1263474Notes

Reaction equation

HRID 1263474 reaction equation
[C:1]([OH:10])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[SH:4].[CH3:11][O:12][C:13]1[CH:20]=[CH:19][C:16]([CH2:17]Cl)=[CH:15][CH:14]=1.O>CN(C)C=O.C([O-])([O-])=O.[K+].[K+]>[CH3:11][O:12][C:13]1[CH:20]=[CH:19][C:16]([CH2:17][S:4][C:3]2[C:2](=[CH:8][CH:7]=[CH:6][CH:5]=2)[C:1]([OH:10])=[O:9])=[CH:15][CH:14]=1

Participants

6

Reactant 3

HCID 962WaterHCID 54432-Mercaptobenzoic AcidHCID 699934-Methyloxybenzyl chloride

Product 1

HCID 3568003Benzoic acid, 2-[[(4-methoxyphenyl)methyl]thio]-Yield 99.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 11430Potassium CarbonateSolvent

Procedure

Thiosalicylic acid 15.419 g(0.1M) was dissolved in 150 mL of dimethylformamide (DMF) and 41.463 g(0.3M) of K2CO3, was added to the mixture with stirring. To the above solution, 4-methoxybenzyl chloride 15.661 g(0.1M) was added and the mixture was refluxed for 10 hours. The solution then was cooled to room temperature and 150 mL of water was added and the mixture was acidified with 3M HCL. The precipitated material was collected by gravity filtration and washed with acetone to give 27.364 g(99.7%) of white powder with a melting point of 225-227° C. and the following specifications:

Workup

  1. temperaturethe mixture was refluxed for 10 hours
  2. filtrationThe precipitated material was collected by gravity filtration
  3. washwashed with acetone

Sources & evidence

ORD record
ord-1a894cffbe01484babe773529d2a4d15
Source dataset
uspto-grants-2003_04
Patent number
US06541479B1

Reaction notes

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