Malonic Acid → 3-(3-Hydroxy-4-methoxyphenyl)prop-2-enoic acid

HRID 2101079Notes

Reaction equation

HRID 2101079 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH:5]=O.C(O)(=O)[CH2:13][C:14]([OH:16])=[O:15]>N1C=CC=CC=1.N1CCCCC1>[OH:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:13][C:14]([OH:16])=[O:15])[CH:7]=[CH:8][C:9]=1[O:10][CH3:11]

Participants

5

Reactant 2

HCID 867Malonic AcidHCID 12127Isovanillin

Product 1

HCID 921263-(3-Hydroxy-4-methoxyphenyl)prop-2-enoic acidYield 104.5%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8082PiperidineSolvent

Conditions

Temperature
120 °C

Procedure

The mixture of 3-hydroxy-4-methoxy-benzaldehyde (30 g) and malonic acid (42 g) in pyridine (80 ml) and piperidine (4 ml) was heated at 120° C. for 6 hours. The solution was cooled to room temperature and concentrated to 20 ml. The residue was dissolved in 500 ml of water and the solution was acidified with concentrated HCl until PH=3. The solid was collected to give 3-(3-Hydroxy-4-methoxy-phenyl)-acrylic acid (40 g). LC-MS: m/e 195 (MH+).

Workup

  1. temperatureThe solution was cooled to room temperature
  2. concentrationconcentrated to 20 ml
  3. dissolutionThe residue was dissolved in 500 ml of water
  4. customThe solid was collected

Sources & evidence

ORD record
ord-9b25810630f84763b5e3590f564e03bc
Source dataset
uspto-grants-2009_08
Patent number
US07572809B2

Reaction notes

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