Dimethyl Sulfate → HCID 20513492, compound

HRID 1164118Notes

Reaction equation

HRID 1164118 reaction equation
[OH-].[K+].[OH:3][C:4]1[C:9]([S:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[F:17])=[CH:8][CH:7]=[CH:6][C:5]=1[CH:18]([OH:20])[CH3:19].S(OC)(O[CH3:25])(=O)=O>O>[CH3:25][O:3][C:4]1[C:9]([S:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[F:17])=[CH:8][CH:7]=[CH:6][C:5]=1[CH:18]([OH:20])[CH3:19]

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 14797Potassium HydroxideHCID 20513426HCID 20513426, compound

Product 1

HCID 20513492HCID 20513492, compoundYield 45.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
60 °C

Procedure

A solution of potassium hydroxide (1.6 g) in water (20 ml) was added slowly to a mixture of 1-[2-hydroxy-3-(2-fluorophenylthio)phenyl]ethanol (2.1 g) and dimethyl sulfate (2 g), and the mixture was stirred at room temperature for 30 minutes and at 60° C. for an hour. To the reaction mixture was added water, and the mixture was extracted with diethyl ether. The extract was washed with dil. aqueous solution of sodium hydroxide and water in turn, dried and evaporated under reduced pressure. The oily residue (1.8 g) was purified by column chromatography (silica gel 30 g, toluene) to give 1-[2-methoxy-3-(2-fluorophenylthio) phenyl]ethanol (1 g).

Workup

  1. extractionthe mixture was extracted with diethyl ether
  2. washThe extract was washed with dil. aqueous solution of sodium hydroxide and water in turn
  3. customdried
  4. customevaporated under reduced pressure
  5. customThe oily residue (1.8 g) was purified by column chromatography (silica gel 30 g, toluene)

Sources & evidence

ORD record
ord-cb3e66b285254d6d864461117411ce03
Source dataset
uspto-grants-1983_01
Patent number
US04367238

Reaction notes

Loading…