Malonic Acid → 3-(3-Chloro-4-hydroxyphenyl)prop-2-enoic acid

HRID 259620Notes

Reaction equation

HRID 259620 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[OH:10])[CH:5]=O.C(O)(=O)[CH2:12][C:13]([OH:15])=[O:14].N1CCCCC1>N1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[OH:10])[CH:5]=[CH:12][C:13]([OH:15])=[O:14]

Participants

5

Reactant 3

HCID 867Malonic AcidHCID 8082PiperidineHCID 170223-Chloro-4-hydroxybenzaldehyde

Product 1

HCID 534257193-(3-Chloro-4-hydroxyphenyl)prop-2-enoic acid

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

46.2 g (0.273 mol) of 3-chloro-4-hydroxy-benzaldehyde, 104 g (1 mol) of malonic acid, 140 ml of pyridine and 4 ml of piperidine are heated to 100° C. for 2 hours, whilst stirring. The volatile constituents are distilled off under reduced pressure at 80° C. and the residue is stirred with 800 ml of water. The resulting crystals are filtered off and recrystallised from methanol-water. 3-Chloro-4-hydroxy-cinnamic acid of melting point 180°-182° C. is obtained.

Workup

  1. distillationThe volatile constituents are distilled off under reduced pressure at 80° C.
  2. stirringthe residue is stirred with 800 ml of water
  3. filtrationThe resulting crystals are filtered off
  4. customrecrystallised from methanol-water

Sources & evidence

ORD record
ord-8a5ed99cda1c46b2be22a8067103736c
Source dataset
uspto-grants-1977_07
Patent number
US04038414

Reaction notes

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