Thionyl Chloride → 2-[(Phenylmethyl)thio]benzoyl chloride

HRID 982294

Reaction equation

HRID 982294 reaction equation
[C:1]1([CH2:7][S:8][C:9]2[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=2[C:11](O)=[O:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(Cl)([Cl:20])=O>C1C=CC=CC=1>[C:1]1([CH2:7][S:8][C:9]2[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=2[C:11]([Cl:20])=[O:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 2641822-(Benzylsulfanyl)benzoic acid

Product 1

HCID 200673402-[(Phenylmethyl)thio]benzoyl chlorideYield 94.1%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A suspension of 100 g of 2-[(phenylmethyl)thio]benzoic acid and 97.6 g of thionyl chloride in 800 ml of benzene was refluxed for about three hours then evaporated to dryness under vacuum. The residue was triturated with hexane to yield 101.2 g of 2-[(phenylmethyl)thio]benzoyl chloride, m.p. 113° to 116° C.

Workup

  1. temperaturewas refluxed for about three hours
  2. customthen evaporated to dryness under vacuum
  3. customThe residue was triturated with hexane

Sources & evidence

ORD record
ord-f6ab892768b743d48204bed41050d080
Source dataset
uspto-grants-1991_02
Patent number
US04995901

Linked notes

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