Benzyl Chloride → HCID 11543171, compound

HRID 342380Notes

Reaction equation

HRID 342380 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[SH:9].CC(C)([O-])C.[K+].[CH2:16](Cl)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>O1CCCC1>[CH2:16]([S:9][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[O:2][CH3:1])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Procedure

A solution of 25.0 g (178 mmol) of 2-methoxy-thiophenol in 50 mL of dry tetrahydrofuran was added dropwise to a mixture of 22.0 g (196 mmol) of potassium t-butoxide and 100 mL of tetrahydrofuran at 0° C. with stirring. A solution of 25 mL (214 mmol) of benzyl chloride in 50 mL of tetrahydrofuran was added to this with stirring and cooling and the mixture was then allowed to warm to ambient temperature and was stirred for 18 hours. The resulting mixture was concentrated by evaporation under reduced pressure and the residue was diluted with 300 mL of dichloromethane. The solution obtained was washed with water, dried over magnesium sulfate, and concentrated by evaporation under reduced pressure. The residue was the title compound, a white solid melting at 69°-70° C.

Workup

  1. stirringthis with stirring
  2. temperaturecooling
  3. stirringwas stirred for 18 hours
  4. concentrationThe resulting mixture was concentrated by evaporation under reduced pressure
  5. additionthe residue was diluted with 300 mL of dichloromethane
  6. customThe solution obtained
  7. washwas washed with water
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated by evaporation under reduced pressure

Sources & evidence

ORD record
ord-3b9de0dcd1644a169606348857e169c7
Source dataset
uspto-grants-1999_01
Patent number
US05858924

Reaction notes

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