Ethyl Acetate → 1-Phenylethanethiol

HRID 731502

Reaction equation

HRID 731502 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]1([CH:13]([S:15]C(=O)C)[CH3:14])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(OCC)(=O)C.[OH-].[Na+]>CC(OC)(C)C>[SH:15][CH:13]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH3:14]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 11126866S-(1-phenylethyl) ethanethioateHCID 21226445Aluminium lithium hydride

Product 1

HCID 1418501-PhenylethanethiolYield 99.3%

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent2×

Procedure

In a synthesis carried out according to Hoppe, et al., Angew. Chem. Int. Ed., 36(24), 2784 (1997), at room temperature, 2.1 g of lithium aluminum hydride and 100 mL of methyl tertiary butyl ether are added to a 250 mL round-bottom flask. To this suspension 18 g of thioacetic acid S-(1-phenyl-ethyl)ester in 50 mL MTBE is added. The mixture is stirred for 15 h at room temperature. 5 mL of ethyl acetate and 2.5 mL of sodium hydroxide (1 M in water) are added. The reaction mixture is filtered over a sodium sulphate plug. The filtrate is concentrated to give 13.7 g of a yellow liquid which is purified by distillation.

Workup

  1. filtrationThe reaction mixture is filtered over a sodium sulphate plug
  2. concentrationThe filtrate is concentrated

Sources & evidence

ORD record
ord-3d4653a7fcd448f080fec43de29e6741
Source dataset
uspto-grants-2009_09
Patent number
US07585535B2

Linked notes

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