2',4'-Dihydroxyacetophenone → HCID 23110664, compound

HRID 1782114Notes

Reaction equation

HRID 1782114 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[C:9](=[O:11])[CH3:10].Br[CH2:13][C:14]([CH3:17])=[CH:15][CH3:16]>[OH-].[K+].CO.CO.[Pd]>[OH:1][C:2]1[C:7]([CH2:16][CH2:15][CH:14]([CH3:17])[CH3:13])=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[C:9](=[O:11])[CH3:10]

Participants

6

Reactant 2

HCID 69902',4'-DihydroxyacetophenoneHCID 521026HCID 521026, compound

Product 1

HCID 23110664HCID 23110664, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 23689386Potassium hydroxide methanolSolvent

Procedure

2′,4′-Dihydroxyacetophenone (manufactured by Wako Pure Chemical Industries, Ltd.) was treated with 1-bromo-2-methyl-2-butene (manufactured by Aldrich) in 2 M KOH/methanol solution under ice-cooling, and thereafter the treated solution was hydrogenated in methanol, in the presence of palladium black (manufactured by Nakalai Tesque, Inc.), to give 2′,4′-dihydroxy-3′-(3-methylbutyl)acetophenone. Subsequently, 2′,4′-dihydroxy-3′-(3-methylbutyl)acetophenone and 4-hydroxybenzaldehyde (manufactured by Aldrich) were subjected to Claisen condensation, to give a yellow substance.

Workup

  1. temperaturecooling

Sources & evidence

ORD record
ord-01f836b342f54dd0904850f3d1fe6486
Source dataset
uspto-grants-2009_03
Patent number
US07498357B2

Reaction notes

Loading…