Dimethyl Sulfate → 2-Methoxy-3-(2-chlorophenylthio)benzaldehyde

HRID 1164078Notes

Reaction equation

HRID 1164078 reaction equation
[OH:1][C:2]1[C:9]([S:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[Cl:17])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].S(OC)(O[CH3:22])(=O)=O>[OH-].[K+]>[CH3:22][O:1][C:2]1[C:9]([S:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[Cl:17])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5]

Participants

4

Reactant 2

HCID 6497Dimethyl SulfateHCID 205134432-Hydroxy-3-(2-chlorophenylthio)benzaldehyde

Product 1

HCID 205134222-Methoxy-3-(2-chlorophenylthio)benzaldehydeYield 45.3%

Reagents, catalysts & solvents 1

HCID 14797Potassium HydroxideSolvent

Procedure

A mixture of 2-hydroxy-3-(2-chlorophenylthio)benzaldehyde (19.3 g) and dimethyl sulfate (18.4 g) was stirred at room temperature. To the mixture was added dropwise an aqueous solution (50 ml) of potassium hydroxide (12.5 g) at temperature below 60° C., and then the mixture was stirred for an hour. The reaction mixture was cooled to the ambient temperature and insoluble substance was filtered off. The filtrate was extracted with diethyl ether, and the extract was washed with water, dried over magnesium sulfate and then evaporated under reduced pressure to give oily 2-methoxy-3-(2-chlorophenylthio)benzaldehyde (9.2 g).

Workup

  1. stirringthe mixture was stirred for an hour
  2. temperatureThe reaction mixture was cooled to the ambient temperature and insoluble substance
  3. filtrationwas filtered off
  4. extractionThe filtrate was extracted with diethyl ether
  5. washthe extract was washed with water
  6. dry with materialdried over magnesium sulfate
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-8fd23be2987848789d8e31e8d523dfd2
Source dataset
uspto-grants-1983_01
Patent number
US04367238

Reaction notes

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