4-Methylbenzaldehyde → HCID 76168092, compound

HRID 597713Notes

Reaction equation

HRID 597713 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].[CH3:16][C:17]1[CH:24]=[CH:23][C:20]([CH:21]=O)=[CH:19][CH:18]=1>N1CCCCC1.C(Cl)(Cl)Cl>[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:24]=[CH:23][C:20]([CH3:21])=[CH:19][CH:18]=2)[C:9]=1[OH:10])(=[O:13])[CH3:12]

Participants

5

Reactant 2

HCID 77254-MethylbenzaldehydeHCID 1354659693,5-Diacetyl-2,6-dihydroxy-4h-pyran-4-one

Product 1

HCID 76168092HCID 76168092, compound

Reagents, catalysts & solvents 2

HCID 8082PiperidineCatalystHCID 6212ChloroformSolvent

Procedure

Following the procedure of Example 1, a mixture of 8.48 g. (0.04 m.) of 3,5-diacetyl-4,6-dihydroxy-2H-pyran-2-one, 4.8 g. (0.04 m.) of p-methylbenzaldehyde in 100 ml. of chloroform and 20 drops of piperidine is refluxed for 10 hours, concentrated and filtered to yield 5-acetyl-4-hydroxy-3-(p-methylcinnamoyl)-2H-pyran-2,6(3H)-dione, m.p. 188°-190° C.

Workup

  1. additiona mixture of 8.48 g
  2. concentrationconcentrated
  3. filtrationfiltered

Sources & evidence

ORD record
ord-3d0bd77d64684663a42fbeb086260ce7
Source dataset
uspto-grants-1977_03
Patent number
US04015009

Reaction notes

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