Thionyl Chloride → 3-Benzoylacrylyl chloride

HRID 894087Notes

Reaction equation

HRID 894087 reaction equation
[C:1]([CH:9]=[CH:10][C:11]([OH:13])=O)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)([Cl:16])=O>C(Cl)Cl>[C:1]([CH:9]=[CH:10][C:11]([Cl:16])=[O:13])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 94714Beta-benzoylacrylic acid

Product 1

HCID 573021923-Benzoylacrylyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Benzoylacrylic acid (3 g.) was refluxed for 2 hours with 100 ml. of methylene chloride and 10 ml. thionyl chloride. Concentration to dryness gave 3-benzoylacrylyl chloride. Methanol (15 ml.) was added and the resulting solution stirred for 0.5 hour. Ether (35 ml.) was added. The resulting organic mixture was washed in sequence with 15 ml. of water, 15 ml. of 1 N sodium hydroxide and twice with 15 ml. of water, concentrated to an oil, the oil triturated with 25 ml. of hot hexane, decanted from insolubles and the hexane concentrated to yield methyl 3-benzoylacrylate (1.9 g., oil, m/e 190).

Workup

  1. concentrationConcentration to dryness

Sources & evidence

ORD record
ord-bbaa47fa523545d9b15c202685f82276
Source dataset
uspto-grants-1981_08
Patent number
US04282242

Reaction notes

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