4-Toluenesulfonyl chloride → Methyl 2-hydroxy-5-{[(4-methylphenyl)sulfonyl]oxy}benzoate

HRID 1623656Notes

Reaction equation

HRID 1623656 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].C(=O)([O-])[O-].[K+].[K+].[S:19](Cl)([C:22]1[CH:28]=[CH:27][C:25]([CH3:26])=[CH:24][CH:23]=1)(=[O:21])=[O:20]>CC(C)=O>[OH:1][C:2]1[CH:11]=[CH:10][C:9]([O:12][S:19]([C:22]2[CH:28]=[CH:27][C:25]([CH3:26])=[CH:24][CH:23]=2)(=[O:21])=[O:20])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 11430Potassium CarbonateHCID 75077Methyl Gentisate

Product 1

HCID 15727852Methyl 2-hydroxy-5-{[(4-methylphenyl)sulfonyl]oxy}benzoate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of methyl 2,5-dihydroxybenzoate (1.5 g, 8.92 mmol), potassium carbonate (7.50 g, 54.2 mmol), and dry acetone (100 ml) was stirred at room temperature for 30 min. To the mixture was added TsCl (1.72 g, 9.00 mmol) portionwise and the mixture was refluxed for 7 h. The reaction mixture was used in the next step directly.

Workup

  1. temperaturethe mixture was refluxed for 7 h

Sources & evidence

ORD record
ord-84de467f8d274fb9b3a510b96ab648b3
Source dataset
uspto-grants-2014_07
Patent number
US08778939B2

Reaction notes

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