Benzaldehyde → 1-Phenyl-1,4-pentanedione

HRID 1198311Notes

Reaction equation

HRID 1198311 reaction equation
C(N(CC)CC)C.[CH2:8]=[CH:9][C:10](=[O:12])[CH3:11].[CH:13](=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>[Cl-].C([N+]1C(C)=C(CCO)SC=1)C1C=CC=CC=1.C(O)C>[C:14]1([C:13](=[O:20])[CH2:8][CH2:9][C:10](=[O:12])[CH3:11])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 3

HCID 240BenzaldehydeHCID 6570Methyl vinyl ketoneHCID 8471Triethylamine

Product 1

HCID 1363711-Phenyl-1,4-pentanedione

Reagents, catalysts & solvents 2

HCID 28333523-Benzyl-5-(2-hydroxyethyl)-4-methylthiazolium chlorideCatalystHCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 8.1 g (0.03 mol) 3-benzyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazolium chloride, 180 ml triethylamine, 150 ml ethanol, 21 g of 1-butene-3-one (0.3 mol) and 30.7 g of benzaldehyde (0.29 mol) was gently stirred at 80° C. for 16 hours. Volatile components were removed by evaporation. The 1-phenyl-1,4-pentanedione thus formed was recovered by extraction and subsequent vacuum distillation.

Workup

  1. customVolatile components were removed by evaporation

Sources & evidence

ORD record
ord-90cbba4aab5545cd868be8f5a9867dbe
Source dataset
uspto-grants-1994_01
Patent number
US05279999

Reaction notes

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