Acetone → 1-[5-(Benzyloxy)-2-hydroxyphenyl]ethan-1-one

HRID 1960171Notes

Reaction equation

HRID 1960171 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[C:8]([OH:10])[CH:7]=[CH:6][C:5]=1[OH:11])=[O:3].[CH2:12](Br)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+].CC(C)=O>O>[CH3:1][C:2]([C:4]1[CH:9]=[C:8]([O:10][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:7]=[CH:6][C:5]=1[OH:11])=[O:3]

Participants

6

Reactant 4

HCID 180AcetoneHCID 7498Benzyl BromideHCID 102792-AcetylhydroquinoneHCID 11430Potassium Carbonate

Product 1

HCID 128709281-[5-(Benzyloxy)-2-hydroxyphenyl]ethan-1-oneYield 41.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2,5-dihydroxyacetophenone (5.00 g, 0.0329 mol), benzyl bromide (3.72 ml, 0.031 mol), potassium carbonate (4.31 g, 0.031 mol) and acetone (150 ml) were added to a 500 ml round bottom flask. The reaction mixture was heated overnight at reflux and then was cooled to ambient temperature. When cool, deionized water (150 ml) was added to the reaction mixture and the reaction mixture was extracted three times with 100 ml portions of diethyl ether. The combined ether layers were dried with sodium sulfate and concentrated in vacuo yielding a dark solid. This dark solid was recrystallized from 50:50 (ethanol:water) yielding 3.09 g of 2-hydroxy-5-benzyloxyacetophenone as yellow needles.

Workup

  1. temperatureThe reaction mixture was heated overnight
  2. temperatureat reflux
  3. temperatureWhen cool
  4. extractionthe reaction mixture was extracted three times with 100 ml portions of diethyl ether
  5. dry with materialThe combined ether layers were dried with sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customyielding a dark solid
  8. customThis dark solid was recrystallized from 50:50 (ethanol:water)

Sources & evidence

ORD record
ord-6996ce8a76ab45eeb58d22b2574fc8d6
Source dataset
uspto-grants-2013_04
Patent number
US08410309B2

Reaction notes

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