Malonic Acid → Benzoic acid, 4-(2-carboxyethenyl)-, methyl ester

HRID 369889Notes

Reaction equation

HRID 369889 reaction equation
[CH:1]([C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][CH:4]=1)=O.C(O)(=O)[CH2:14][C:15]([OH:17])=[O:16].N1CCCCC1>N1C=CC=CC=1>[CH3:10][O:9][C:7]([C:6]1[CH:11]=[CH:12][C:3]([CH:1]=[CH:14][C:15]([OH:17])=[O:16])=[CH:4][CH:5]=1)=[O:8]

Participants

5

Reactant 3

HCID 867Malonic AcidHCID 8082PiperidineHCID 15294Methyl 4-Formylbenzoate

Product 1

HCID 86881Benzoic acid, 4-(2-carboxyethenyl)-, methyl esterYield 94.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of methyl p-formylbenzoate (12.33 g), malonic acid (16 g) and piperidine (1 ml) in pyridine (100 ml) is refluxed for two hours. The reaction mixture is poured into ice-water, and the precipitated white powder is collected by filtration, and washed with water, and dried to give 4-methoxycarbonyl cinnamic acid (14.7 g).

Workup

  1. filtrationthe precipitated white powder is collected by filtration
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-d212a7e67ecd4cf78cf6818eea2092bf
Source dataset
uspto-grants-2000_10
Patent number
US06140330

Reaction notes

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