Dimethyl Sulfate → 2-Methoxy-3-(o-tolylthio)benzyl alcohol

HRID 1164108Notes

Reaction equation

HRID 1164108 reaction equation
[OH-].[K+].[OH:3][C:4]1[C:11]([S:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[CH3:19])=[CH:10][CH:9]=[CH:8][C:5]=1[CH2:6][OH:7].S(OC)(O[CH3:24])(=O)=O>O>[CH3:24][O:3][C:4]1[C:11]([S:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[CH3:19])=[CH:10][CH:9]=[CH:8][C:5]=1[CH2:6][OH:7]

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 14797Potassium HydroxideHCID 130666702-Hydroxy-3-(o-tolylthio)benzyl alcohol

Product 1

HCID 545312442-Methoxy-3-(o-tolylthio)benzyl alcoholYield 96.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of potassium hydroxide (5.8 g) in water (30 ml) was added dropwise to a mixture of 2-hydroxy-3-(o-tolylthio)benzyl alcohol (8.3 g) and dimethyl sulfate (8.5 g) in 10 minutes at temperature below 60° C. with stirring, and the mixture was stirred at the same temperature for 10 minutes. The reaction mixture was treated in a similar manner to that of Example 21-(4). The resultant oily residue was purified by column chromatography (silica gel 150 g, benzene) to give oily 2-methoxy-3-(o-tolylthio)benzyl alcohol (8.5 g).

Workup

  1. stirringthe mixture was stirred at the same temperature for 10 minutes
  2. additionThe reaction mixture was treated in a similar manner to that of Example 21-(4)
  3. customThe resultant oily residue was purified by column chromatography (silica gel 150 g, benzene)

Sources & evidence

ORD record
ord-1f157c32e06d4a0898ea18f4306e1ecc
Source dataset
uspto-grants-1983_01
Patent number
US04367238

Reaction notes

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