Hydrochloric Acid → 3-(3-Chloro-4-fluorophenyl)prop-2-enoic acid

HRID 1579209Notes

Reaction equation

HRID 1579209 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[F:10])[CH:5]=O.C(O)(=O)[CH2:12][C:13]([OH:15])=[O:14].N1CCCCC1.Cl>N1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[F:10])[CH:5]=[CH:12][C:13]([OH:15])=[O:14]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 867Malonic AcidHCID 8082PiperidineHCID 5938663-Chloro-4-fluorobenzaldehyde

Product 1

HCID 27736443-(3-Chloro-4-fluorophenyl)prop-2-enoic acid

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A stirred mixture of 3-chloro-4-fluorobenzaldehyde (55 g, 0.35 mole), malonic acid (47 g, 0.45 mole) and 3.5 ml of piperidine in 138 ml of pyridine was heated on a steam bath for 2 hours. The reaction solution was poured into a mixture of 200 ml of concentrated hydrochloric acid and 320 g of ice to give after filtration and water wash 44 g (63%). The crude intermediate was used without further purification in part D.

Workup

  1. temperaturewas heated on a steam bath for 2 hours
  2. customto give
  3. filtrationafter filtration and water
  4. washwash 44 g (63%)
  5. customThe crude intermediate was used without further purification in part D

Sources & evidence

ORD record
ord-6e84c6e231964b91a5231f32311e659c
Source dataset
uspto-grants-1976_01
Patent number
US03931168

Reaction notes

Loading…