2',4'-Dihydroxyacetophenone → 1-(2,4-Bis(benzyloxy)phenyl)ethanone

HRID 1433165Notes

Reaction equation

HRID 1433165 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:9][C:10]([C:12]1[CH:13]=[CH:14][C:15]([OH:19])=[CH:16][C:17]=1[OH:18])=[O:11].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH2:1]([O:18][C:17]1[CH:16]=[C:15]([O:19][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:14]=[CH:13][C:12]=1[C:10](=[O:11])[CH3:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 69902',4'-DihydroxyacetophenoneHCID 7498Benzyl BromideHCID 11430Potassium Carbonate

Product 1

HCID 3194691-(2,4-Bis(benzyloxy)phenyl)ethanoneYield 78.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Benzyl bromide (35.6 mL, 0.3 mol) was added to a suspension of 2,4-dihydroxyacetophenone (15 g, 0.1 mol) and potassium carbonate (41.4 g, 0.3 mol) in acetonitrile (150 mL) and the mixture stirred overnight. After concentration to dryness, the residues were resuspended in dichloromethane (100 mL) and washed with water (100 mL). The organic phase was dried over magnesium sulphate and concentrated. Trituration with hexanes, filtration and drying in vacuo gave 1-(2,4-Bis-benzyloxyphenyl)-ethanone as a white powder (26 g).

Workup

  1. concentrationAfter concentration to dryness
  2. washwashed with water (100 mL)
  3. dry with materialThe organic phase was dried over magnesium sulphate
  4. concentrationconcentrated
  5. filtrationTrituration with hexanes, filtration
  6. customdrying in vacuo

Sources & evidence

ORD record
ord-212986c9f09d4442b78e2ee936d40c87
Source dataset
uspto-grants-2009_11
Patent number
US07612201B2

Reaction notes

Loading…