Dimethyl Sulfate → HCID 53999561, compound

HRID 1164090Notes

Reaction equation

HRID 1164090 reaction equation
S(OC)(O[CH3:5])(=O)=O.[OH:8][C:9]1[C:16]([S:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[Cl:24])=[CH:15][CH:14]=[CH:13][C:10]=1[CH2:11][OH:12].[OH-].[K+]>O>[CH3:5][O:8][C:9]1[C:16]([S:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[Cl:24])=[CH:15][CH:14]=[CH:13][C:10]=1[CH2:11][OH:12]

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 14797Potassium HydroxideHCID 539316392-Hydroxy-3-(2-chlorophenylthio)benzyl alcohol

Product 1

HCID 53999561HCID 53999561, compoundYield 96.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Dimethyl sulfate (5.7 g) was added to a mixture of 2-hydroxy-3-(2-chlorophenylthio)benzyl alcohol (6 g) and potassium hydroxide (3.8 g) in water (20 ml) in 10 minutes with stirring. The mixture was stirred at 50° C. for 1.5 hours, and the reaction mixture was treated in a similar manner to that of Example 21-(4) to give oily 2-methoxy-3-(2-chlorophenylthio)benzyl alcohol (6.1 g). This product was purified by column chromatography (silica gel 100 g, benzene-ethyl acetate 10:1) to give purified oily substance (5.6 g). This product was identified with the compound obtained in Example 21-(5) by IR and NMR spectrum.

Workup

  1. stirringThe mixture was stirred at 50° C. for 1.5 hours
  2. additionthe reaction mixture was treated in a similar manner to that of Example 21-(4)

Sources & evidence

ORD record
ord-1c04ef9b9b31460ca5fe6e1939921135
Source dataset
uspto-grants-1983_01
Patent number
US04367238

Reaction notes

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