1-Phenylethanol → S-(1-phenylethyl) ethanethioate

HRID 731501Notes

Reaction equation

HRID 731501 reaction equation
[C:1]1([CH:7](O)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:10]([OH:13])(=[S:12])[CH3:11]>[I-].[Zn+2].[I-].ClCCl>[C:1]1([CH:7]([S:12][C:10](=[O:13])[CH3:11])[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 74091-PhenylethanolHCID 178418634HCID 178418634, compound

Product 1

HCID 11126866S-(1-phenylethyl) ethanethioateYield 98.7%

Reagents, catalysts & solvents 2

HCID 9883512zinc(II)iodideCatalystHCID 6344DichloromethaneSolvent

Procedure

In a synthesis carried our according to Gauthier, Bourdon, Young, Tetrahedron Lett., 27(1), 15 (1986), at room temperature, 16.3 g of zinc iodide, 100 mL of dichloromethane and 12.5 g of 1-Phenyl-1-ethylalcohol are added to a 250 ml round-bottom flask. To this suspension 9.52 g of thioacetic acid is added. The mixture is stirred for 16 hours at room temperature. The reaction mixture is extracted with dichloromethane. The organic layer is washed with brine, dried over magnesium sulphate, filtered and concentrated to give 18.2 g of a yellow liquid which is purified by chromatography on silica gel.

Workup

  1. extractionThe reaction mixture is extracted with dichloromethane
  2. washThe organic layer is washed with brine
  3. dry with materialdried over magnesium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-e5ee46882bdc4ee1b564f5e54c6424a4
Source dataset
uspto-grants-2009_09
Patent number
US07585535B2

Reaction notes

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