Malonic Acid → 3-(3,5-Dimethoxyphenyl)prop-2-enoic acid

HRID 2100743Notes

Reaction equation

HRID 2100743 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([O:11][CH3:12])[CH:10]=1)[CH:6]=O.C(O)(=O)[CH2:14][C:15]([OH:17])=[O:16].N1CCCCC1>N1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:6]=[CH:14][C:15]([OH:17])=[O:16])[CH:8]=[C:9]([O:11][CH3:12])[CH:10]=1

Participants

5

Reactant 3

HCID 867Malonic AcidHCID 8082PiperidineHCID 817473,5-Dimethoxybenzaldehyde

Product 1

HCID 860923-(3,5-Dimethoxyphenyl)prop-2-enoic acidYield 91.8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 3,5-Dimethoxy-benzaldehyde (9.5 g, 57.17 mmol) in pyridine (60 ml), malonic acid (9 g, 85.725 mmol) was added, and followed by piperidine (2 ml), the mixture was heated to 100° C. and stirred at this temperature for 6 hs under N2. Then most of pridine was removed, and the residue was poured into water (250 ml), acidified to PH=3 by aq.HCl, the precipitate was collected and dried to give product (10.9 g, 91.8%). LC-MS: m/e 207 (M−1)

Workup

  1. customThen most of pridine was removed
  2. additionthe residue was poured into water (250 ml)
  3. customHCl, the precipitate was collected
  4. customdried

Sources & evidence

ORD record
ord-4d7c34d31c7348f293ea655d6c3bdc4a
Source dataset
uspto-grants-2009_08
Patent number
US07572809B2

Reaction notes

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