Hydrochloric Acid → 3-(3-Chlorophenyl)prop-2-enoic acid

HRID 25968

Reaction equation

HRID 25968 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=O.C(O)(=O)[CH2:11][C:12]([OH:14])=[O:13].N1C=CC=CC=1.Cl>O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[CH:11][C:12]([OH:14])=[O:13]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 867Malonic AcidHCID 1049PyridineHCID 114773-Chlorobenzaldehyde

Product 1

HCID 746313-(3-Chlorophenyl)prop-2-enoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The starting material is prepared as follows: The mixture of 50 g of 3-chlorobenzaldehyde, 41 g of malonic acid and 36 ml of pyridine is heated on the steam bath for 3 hours. The residue is dissolved in 200 ml of water, the solution acidified with hydrochloric acid, filtered, and the residue recrystallized from aqueous ethanol, to yield the 3-chlorocinnamic acid melting at 150°-152°.

Workup

  1. customThe starting material is prepared
  2. temperatureis heated on the steam bath for 3 hours
  3. filtrationfiltered
  4. customthe residue recrystallized from aqueous ethanol

Sources & evidence

ORD record
ord-bdef277686ca4cf78ffde5dfc821e56d
Source dataset
uspto-grants-1979_04
Patent number
US04147786

Linked notes

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