Thionyl Chloride → o-(2',5'-Dimethylbenzoylvinyl)benzoyl chloride

HRID 65607Notes

Reaction equation

HRID 65607 reaction equation
[CH3:1][C:2]1[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][C:3]=1[C:4](=[O:16])[CH2:5][CH:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:8](=O)[O:7]1.S(Cl)([Cl:24])=O>C1C=CC=CC=1>[CH3:1][C:2]1[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][C:3]=1[C:4]([CH:5]=[CH:6][C:15]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:8]([Cl:24])=[O:7])=[O:16]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 164335533-[2-(2,5-Dimethylphenyl)-2-oxoethyl]-1,3-dihydro-2-benzofuran-1-one

Product 1

HCID 86736187o-(2',5'-Dimethylbenzoylvinyl)benzoyl chloride

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A 1 liter flask was charged with 32.2 grams (115 mmol) of 3-(2',5'-dimethylphenacyl)phthalide, 200 ml of benzene and 50 ml of thionyl chloride. After heating at reflux on a steambath for 30 minutes, the solution was concentrated. The residue was triturated with ligroin to give 32.5 grams of o-(2',5'-dimethylbenzoylvinyl)benzoyl chloride, m.p. 96°-98° C. Analysis shows 72.29% carbon, 5.07% hydrogen and 11.80% chlorine as against calculated values of 72.36%, 5.06% and 11.87% for C18H15ClO2.

Workup

  1. temperatureAfter heating
  2. temperatureat reflux on a steambath for 30 minutes
  3. concentrationthe solution was concentrated
  4. customThe residue was triturated with ligroin

Sources & evidence

ORD record
ord-1e96314ef7384032ad7a5ce84c2278f4
Source dataset
uspto-grants-1978_12
Patent number
US04128576

Reaction notes

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