Acetic Acid → HCID 398895, compound

HRID 247876Notes

Reaction equation

HRID 247876 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:10]=[C:11]([C:14]([CH3:17])([CH3:16])[CH3:15])[C:12]=1[OH:13])[CH:8]=O)([CH3:4])([CH3:3])[CH3:2].[NH:18]1[CH2:24][C:22](=[O:23])[NH:21][C:19]1=[O:20].NCCC(O)=O.C(O)(=O)C>O>[CH3:16][C:14]([C:11]1[CH:10]=[C:7]([CH:8]=[C:24]2[NH:18][C:19](=[O:20])[NH:21][C:22]2=[O:23])[CH:6]=[C:5]([C:1]([CH3:3])([CH3:2])[CH3:4])[C:12]=1[OH:13])([CH3:15])[CH3:17]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 239Beta-AlanineHCID 10006HydantoinHCID 732193,5-Di-tert-butyl-4-hydroxybenzaldehyde

Product 1

HCID 398895HCID 398895, compoundYield 50.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3,5-di-t-butyl-4-hydroxybenzaldehyde 7.0 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 48 hours the mixture is stirred into water (300 ml), and the precipitate is filtered off, rinsed with water three times, and dried. Recrystallization from acetonitrile gave the pure product (4.8 g), mp 251°-252° C.

Workup

  1. temperatureheated to reflux
  2. filtrationthe precipitate is filtered off
  3. washrinsed with water three times
  4. customdried
  5. customRecrystallization from acetonitrile

Sources & evidence

ORD record
ord-e3c2242b72f44d008c773a78cba86383
Source dataset
uspto-grants-1993_05
Patent number
US05208250

Reaction notes

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