Malonic Acid → 3-(4-Hydroxy-3-Methoxyphenyl)Prop-2-Enoic Acid

HRID 2100733Notes

Reaction equation

HRID 2100733 reaction equation
O=[CH:2][C:3]1[CH:11]=[CH:10][C:8]([OH:9])=[C:5]([O:6][CH3:7])[CH:4]=1.C(O)(=O)[CH2:13][C:14]([OH:16])=[O:15].N1CCCCC1>N1C=CC=CC=1>[OH:9][C:8]1[CH:10]=[CH:11][C:3]([CH:2]=[CH:13][C:14]([OH:16])=[O:15])=[CH:4][C:5]=1[O:6][CH3:7]

Participants

5

Reactant 3

HCID 867Malonic AcidHCID 1183VanillinHCID 8082Piperidine

Product 1

HCID 7093-(4-Hydroxy-3-Methoxyphenyl)Prop-2-Enoic AcidYield 92%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
90 °C

Procedure

Vanillin (40 g, 263 mmol) was dissolved in pyridine (120 ml), and malonic acid (41 g, 395 mm ol) was added, followed by piperidine (4 ml). The mixture was heated at 90° C. for 6 hs under N2. After removal of pridine, the residue was poured into water (500 ml), acidified to PH=3 by aq.HCl. The precipitate was collected, washed by water (150 ml×3), and dried to give product (47 g, 91.8%). LC-MS: m/e 193 (M−1)

Workup

  1. customAfter removal of pridine
  2. additionthe residue was poured into water (500 ml)
  3. customThe precipitate was collected
  4. washwashed by water (150 ml×3)
  5. customdried

Sources & evidence

ORD record
ord-5e0eb99ab5934ef0818057a3f0631337
Source dataset
uspto-grants-2009_08
Patent number
US07572809B2

Reaction notes

Loading…