Ethyl benzoate → Ethyl thiobenzoate

HRID 915682Notes

Reaction equation

HRID 915682 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>[CH2:10]([O:9][C:1](=[S:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH3:11]

Participants

4

Reactant 2

HCID 7165Ethyl benzoateHCID 87949Lawesson's reagent

Product 1

HCID 578278Ethyl thiobenzoateYield 115.3%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

Prepare a solution of ethyl benzoate (10 g, 66.5 mmol) in xylene (100 mL). Add Lawesson's reagent (14.5 g, 36 mmol). Reflux the reaction for 5 hours, then concentrate in vacuo to an oil. Chromatograph (silica gel, 100% Hexane) to afford thiobenzoic acid O-ethyl ester (6.9 g). 1H NMR (CDCl3) δ 8.20 (d, J=8 Hz, 2H), 7.52 (t, J=7 Hz, 1H), 7.39 (t, J=7 Hz, 2H), 4.69-4.78 (m, 2H), 1.55 (t, J=7 Hz, 3H).

Workup

  1. temperatureReflux
  2. customthe reaction for 5 hours
  3. concentrationconcentrate in vacuo to an oil

Sources & evidence

ORD record
ord-d66b5c94edc345b0b0d8bac2197c9978
Source dataset
uspto-grants-2007_09
Patent number
US07265246B2

Reaction notes

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