Acetic Acid → HCID 291123, compound

HRID 128735Notes

Reaction equation

HRID 128735 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][C:3]=1[O:10][CH3:11].[NH:12]1[CH2:18][C:16](=[O:17])[NH:15][C:13]1=[O:14].NCCC(O)=O.C(O)(=O)C>O>[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[C:18]2[NH:12][C:13](=[O:14])[NH:15][C:16]2=[O:17])=[CH:4][C:3]=1[O:10][CH3:11]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 239Beta-AlanineHCID 1183VanillinHCID 10006Hydantoin

Product 1

HCID 291123HCID 291123, compoundYield 42.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4-hydroxy-3-methoxybenzaldehyde (4.6 g, 30 mmoles), hydantoin (3.0 g, 30 mmoles), β-alanine (1.4 g, 16 mmoles), and acetic acid (40 ml) is stirred under an inert atmosphere and heated to reflux. After 4 hours the mixture is stirred into water (350 ml) and the precipitate is filtered off, rinsed successively with water (3X), ethanol (2X), and ether (2X), and dried. Recrystallization from methanol afforded the pure product (3.0 g), mp 272°-273° C.

Workup

  1. temperatureheated to reflux
  2. filtrationthe precipitate is filtered off
  3. washrinsed successively with water (3X), ethanol (2X), and ether (2X)
  4. customdried
  5. customRecrystallization from methanol

Sources & evidence

ORD record
ord-1b54489de7de41f3a8ce65b641fabe5d
Source dataset
uspto-grants-1995_11
Patent number
US05464856

Reaction notes

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