Benzaldehyde → HCID 76168097, compound

HRID 1764739Notes

Reaction equation

HRID 1764739 reaction equation
[C:1]([C:4]1[C:5](=[O:15])[O:6][C:7]([OH:14])=[C:8]([C:11](=[O:13])[CH3:12])[C:9]=1[OH:10])(=[O:3])[CH3:2].[CH:16](=O)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(Cl)(Cl)Cl>N1CCCCC1.O>[C:11]([C:8]1[C:7](=[O:14])[O:6][C:5](=[O:15])[CH:4]([C:1](=[O:3])[CH:2]=[CH:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:9]=1[OH:10])(=[O:13])[CH3:12]

Participants

6

Reactant 3

HCID 240BenzaldehydeHCID 6212ChloroformHCID 1354659693,5-Diacetyl-2,6-dihydroxy-4h-pyran-4-one

Product 1

HCID 76168097HCID 76168097, compound

Reagents, catalysts & solvents 2

HCID 8082PiperidineCatalystHCID 962WaterSolvent

Procedure

A mixture of 4.24 g. of 3,5-diacetyl-4,6-dihydroxy-2H-pyran-2-one, 2.12 g. of benzaldehyde, 20 drops of piperidine and 75 ml. of chloroform is refluxed for eight hours. The water liberated during the reaction is removed by a receiver. The reaction mixture is concentrated and triturated with ethanol to afford 5-acetyl-3-cinnamoyl-4-hydroxy-2H-pyran-2,6(3H)-dione, m.p. 154°-155° C.

Workup

  1. additionA mixture of 4.24 g
  2. customis removed by a receiver
  3. concentrationThe reaction mixture is concentrated
  4. customtriturated with ethanol

Sources & evidence

ORD record
ord-07ce02b0137341ed98400260c4c7b0cb
Source dataset
uspto-grants-1978_09
Patent number
US04117226

Reaction notes

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