Malonic Acid → 3-(3-Ethoxy-4-hydroxyphenyl)prop-2-enoic acid

HRID 53832

Reaction equation

HRID 53832 reaction equation
[C:1]([OH:7])(=[O:6])[CH2:2][C:3](O)=O.[CH2:8]([O:10][C:11]1[CH:12]=[C:13]([CH:16]=[CH:17][C:18]=1[OH:19])C=O)[CH3:9].NC1C=CC=CC=1.S(=O)(=O)(O)O>N1C=CC=CC=1>[CH2:8]([O:10][C:11]1[CH:12]=[C:13]([CH:16]=[CH:17][C:18]=1[OH:19])[CH:3]=[CH:2][C:1]([OH:7])=[O:6])[CH3:9]

Participants

6

Reactant 4

HCID 867Malonic AcidHCID 1118Sulfuric AcidHCID 6115AnilineHCID 8467Ethylvanillin

Product 1

HCID 534017043-(3-Ethoxy-4-hydroxyphenyl)prop-2-enoic acidYield 56.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Malonic acid (1.56 g) and pyridine (3.0 ml) were placed in an egg-plant type flask (100 ml). Further, 3-ethoxy-4-hydroxybenzaldehyde (1.66 g) and aniline (30 μl) were added thereto and a reaction was performed at 55° C. for 3 hours. The reaction solution was acidified by adding dilute sulfuric acid. The crude crystals were obtained by filtration, washed with water, and then dried to obtain the above-identified compound (1.1 g, 56.1%) as a light yellowish crystal. Melting point: 157°-158° C.

Workup

  1. customThe crude crystals were obtained by filtration
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-497d9d70153746f4a8ae84d7bcf9cb93
Source dataset
uspto-grants-1997_04
Patent number
US05621009

Linked notes

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