Malonic Acid → 3-Allyl-4-hydroxy-cinnamic acid

HRID 597663Notes

Reaction equation

HRID 597663 reaction equation
C(O[C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][C:12]=1[OH:13])[CH:8]=O)C=C.[C:14]([OH:20])(=[O:19])[CH2:15]C(O)=O.N1CC[CH2:24][CH2:23][CH2:22]1>N1C=CC=CC=1>[CH2:24]([C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][C:12]=1[OH:13])[CH:8]=[CH:15][C:14]([OH:20])=[O:19])[CH:23]=[CH2:22]

Participants

5

Reactant 3

HCID 867Malonic AcidHCID 8082PiperidineHCID 155743773-(Allyloxy)-4-hydroxybenzaldehyde

Product 1

HCID 540628753-Allyl-4-hydroxy-cinnamic acid

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

48.5 g (0.27 mol) of 3-allyloxy-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 crystals obtained are filtered off and recrystallised from methylene chloride. 3-Allyl-4-hydroxy-cinnamic acid of melting point 132°-133° 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. customThe crystals obtained
  4. filtrationare filtered off
  5. customrecrystallised from methylene chloride

Sources & evidence

ORD record
ord-a06bdec0613d451da888b53ca52e0ae4
Source dataset
uspto-grants-1977_03
Patent number
US04014920

Reaction notes

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