Ethyl benzoate → Ethyl thiobenzoate

HRID 1085822Notes

Reaction equation

HRID 1085822 reaction equation
[C:1]([O:9][CH2:10][CH3:11])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:21])=CC=1>C1(C)C(C)=CC=CC=1.CCCCCC>[C:1]([O:9][CH2:10][CH3:11])(=[S:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 7165Ethyl benzoateHCID 87949Lawesson's reagent

Product 1

HCID 578278Ethyl thiobenzoateYield 175.3%

Reagents, catalysts & solvents 2

HCID 7237O-XyleneSolventHCID 8058HexaneSolvent

Procedure

70 ml (0.487 mol) of ethyl benzoate were heated to reflux for 12 hours with 100 g (0.247 mol) of Lawesson reagent in 350 ml of xylene. After cooling to 20° the reaction mixture was diluted with 500 ml of hexane and filtered. The filtrate was flash-chromatographed on 1 kg of silica gel. Elution was carried out with hexane. The fractions which were pure according to the thin-layer chromatogram (eluent: toluene) were combined and evaporated under reduced pressure. There were obtained 72 g (89%) of O-ethyl thiobenzoate as a dark yellow evil-smelling oil which was used without further purification.

Workup

  1. temperatureAfter cooling to 20° the reaction mixture
  2. filtrationfiltered
  3. customThe filtrate was flash-chromatographed on 1 kg of silica gel
  4. washElution
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-60f21de00efe432b81cb570dedd9c6da
Source dataset
uspto-grants-1991_04
Patent number
US05011849

Reaction notes

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