Isoamyl acetoacetate → Isoamyl-alpha-acetyl-3-methoxy-4-hydroxy-5-isopropyl-cinnamate

HRID 1374492Notes

Reaction equation

HRID 1374492 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([CH:12]([CH3:14])[CH3:13])[C:10]=1[OH:11])[CH:6]=O.[C:15]([O:21][CH2:22][CH2:23][CH:24]([CH3:26])[CH3:25])(=[O:20])[CH2:16][C:17]([CH3:19])=[O:18].N1(CC(O)=O)CCCCC1>C1C=CC=CC=1>[CH2:22]([O:21][C:15](=[O:20])[C:16]([C:17](=[O:18])[CH3:19])=[CH:6][C:5]1[CH:8]=[C:9]([CH:12]([CH3:14])[CH3:13])[C:10]([OH:11])=[C:3]([O:2][CH3:1])[CH:4]=1)[CH2:23][CH:24]([CH3:26])[CH3:25]

Participants

5

Reactant 3

HCID 61296Isoamyl acetoacetateHCID 201097Piperidin-1-yl-acetic acidHCID 226079643-Methoxy-4-hydroxy-5-isopropyl benzaldehyde

Product 1

HCID 67318693Isoamyl-alpha-acetyl-3-methoxy-4-hydroxy-5-isopropyl-cinnamate

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Condensation of 3-methoxy-4-hydroxy-5-isopropyl benzaldehyde with isoamyl acetoacetate in the presence of piperidine-acetic acid and benzene as the reaction medium at reflux temperature under continuous azeotropic water removal yields the title product. The reaction takes about 4 hrs for completion. The yield obtained is typically 90–95%.

Workup

  1. temperatureat reflux temperature under continuous azeotropic water
  2. customremoval

Sources & evidence

ORD record
ord-29fecc479f2141cb9f2cb8259e8ac85a
Source dataset
uspto-grants-2007_01
Patent number
US07166273B2

Reaction notes

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