Thionyl Chloride → 3-Methoxycinnamoyl Chloride

HRID 1759516Notes

Reaction equation

HRID 1759516 reaction equation
S(Cl)([Cl:3])=O.[CH3:5][O:6][C:7]1[CH:8]=[C:9]([CH:15]=[CH:16][CH:17]=1)[CH:10]=[CH:11][C:12](O)=[O:13]>C1C=CC=CC=1>[CH3:5][O:6][C:7]1[CH:8]=[C:9]([CH:15]=[CH:16][CH:17]=1)[CH:10]=[CH:11][C:12]([Cl:3])=[O:13]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 871552-Propenoic acid, 3-(3-methoxyphenyl)-

Product 1

HCID 543303913-Methoxycinnamoyl Chloride

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Thionyl chloride (38 g.) was added dropwise to a mixture of 3-methoxycinnamic acid (50 g.) and benzene (500 ml.), and the resulting mixture was heated under reflux for 1.5 hours, then evaporated under reduced pressure on a rotary evaporator to give an oil. The oil solidified on standing at room temperature, giving 59 g. of the product. Analytical sample (m.p. 43°-45° ) was obtained by recrystallization from petroleum ether.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 1.5 hours
  3. customevaporated under reduced pressure on a rotary evaporator
  4. customto give an oil
  5. customon standing at room temperature
  6. customgiving 59 g

Sources & evidence

ORD record
ord-9f8575871aad47c0a283244f739512b5
Source dataset
uspto-grants-1982_07
Patent number
US04341718

Reaction notes

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