3-(p-Tolyl)acrylic acid → p-Methylcinnamoyl chloride

HRID 978470Notes

Reaction equation

HRID 978470 reaction equation
[CH3:1][C:2]1[CH:12]=[CH:11][C:5]([CH:6]=[CH:7][C:8](O)=[O:9])=[CH:4][CH:3]=1.S(Cl)([Cl:15])=O>C(Cl)Cl>[CH3:1][C:2]1[CH:12]=[CH:11][C:5]([CH:6]=[CH:7][C:8]([Cl:15])=[O:9])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 158353-(p-Tolyl)acrylic acidHCID 24386Thionyl Chloride

Product 1

HCID 53411298p-Methylcinnamoyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred mixture of 100 g (0.62 moles) p-methylcinnamic acid in methylene chloride (about 30 ml), 88 g (0.74 moles) thionyl chloride was added dropwise. The reaction mixture was then refluxed for 24 hours. The methylene chloride was removed under reduced pressure and heat to give the corresponding p-methylcinnamic acid chloride. Fresh methylene chloride was added to the acid chloride; half of which was used in Step (b).

Workup

  1. additionwas added dropwise
  2. temperatureThe reaction mixture was then refluxed for 24 hours
  3. customThe methylene chloride was removed under reduced pressure
  4. temperatureheat

Sources & evidence

ORD record
ord-1c87f55dd2ee4ea9873ee59ef4e401bf
Source dataset
uspto-grants-1987_05
Patent number
US04665093

Reaction notes

Loading…