Hydrochloric Acid → o-(4'-Nitrobenzoylvinyl)benzoyl chloride

HRID 65606Notes

Reaction equation

HRID 65606 reaction equation
[N+:1]([C:4]1[CH:22]=[CH:21][C:7]([C:8](=[O:20])[CH2:9][CH:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:12](=O)[O:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].S(Cl)([Cl:25])=O.Cl>C1C=CC=CC=1>[N+:1]([C:4]1[CH:22]=[CH:21][C:7]([C:8]([CH:9]=[CH:10][C:19]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[C:12]([Cl:25])=[O:11])=[O:20])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 24386Thionyl ChlorideHCID 27313943-(4-Nitrophenacyl)Phthalide

Product 1

HCID 86736186o-(4'-Nitrobenzoylvinyl)benzoyl chloride

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A 500 ml flask fitted with a reflux condenser was charged with 29.7 grams (0.1 mol) of 3-(4-nitrophenacyl)phthalide, 0.12 mol of freshly distilled thionyl chloride and 100 ml of benzene. The mixture was heated to reflux temperature on a steambath, and a clear solution formed on initiation of refluxing, with evolution of HCl. The evolution ceased after 1 hour, after which benzene and excess unreacted thionyl chloride were distilled off under reduced pressure. The residual solid in the flask was triturated with ligroin, filtered and dried to yield o-(4'-nitrobenzoylvinyl)benzoyl chloride, m.p. 133°-134° C. Analysis shows 59.4% carbon, 3.36% hydrogen, 4.56% nitrogen and 11.72% chlorine as against calculated values of 60.87%, 3.19%, 4.44% and 11.23% for C16H10ClNO4.

Workup

  1. customA 500 ml flask fitted with a reflux condenser
  2. temperatureThe mixture was heated
  3. temperatureto reflux temperature on a steambath
  4. customa clear solution formed on initiation
  5. distillationafter which benzene and excess unreacted thionyl chloride were distilled off under reduced pressure
  6. customThe residual solid in the flask was triturated with ligroin
  7. filtrationfiltered
  8. customdried

Sources & evidence

ORD record
ord-c46fb3716a394ea989f4752f3cba4610
Source dataset
uspto-grants-1978_12
Patent number
US04128576

Reaction notes

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