Butyryl chloride → Thiobutyric acid S-(1-phenyl-ethyl)ester

HRID 731503Notes

Reaction equation

HRID 731503 reaction equation
[SH:1][CH:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH3:3].[C:10](Cl)(=[O:14])[CH2:11][CH2:12][CH3:13]>>[C:4]1([CH:2]([S:1][C:10](=[O:14])[CH2:11][CH2:12][CH3:13])[CH3:3])[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

3

Reactant 2

HCID 8855Butyryl chlorideHCID 1418501-Phenylethanethiol

Product 1

HCID 86595377Thiobutyric acid S-(1-phenyl-ethyl)esterYield 98%

Procedure

At room temperature, 13.8 g of 1-mercapto-1-phenylethane is dissolved in 50 mL of butyryl chloride. The mixture is stirred at room temperature for 6 hours. It is then cooled down to 0° C. and the reaction is quenched by careful addition of 100 ml of dry methanol in small portions. The mixture is then washed with bicarbonate, dried over magnesium sulfate, filtered and concentrated to give the butyrated compound in 98% yield.

Workup

  1. temperatureIt is then cooled down to 0° C.
  2. customthe reaction is quenched by careful addition of 100 ml of dry methanol in small portions
  3. washThe mixture is then washed with bicarbonate
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give the butyrated compound in 98% yield

Sources & evidence

ORD record
ord-495643dbcb4a4b69880cb975f4aba0a8
Source dataset
uspto-grants-2009_09
Patent number
US07585535B2

Reaction notes

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