2',4'-Dihydroxyacetophenone → 4'-Benzyloxy-2'-hydroxyacetophenone

HRID 1453113Notes

Reaction equation

HRID 1453113 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH2:7](Br)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[OH:15][C:16]1[CH:21]=[C:20]([OH:22])[CH:19]=[CH:18][C:17]=1[C:23](=[O:25])[CH3:24]>CN(C=O)C>[CH2:7]([O:22][C:20]1[CH:19]=[CH:18][C:17]([C:23](=[O:25])[CH3:24])=[C:16]([OH:15])[CH:21]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

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

Product 1

HCID 3092574'-Benzyloxy-2'-hydroxyacetophenoneYield 60.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Potassium carbonate (27.2 g, 0.2 mol) followed by benzyl bromide (7.04 mL, 59.2 mmol) were added to a solution of 1-(2,4-dihydroxy-phenyl)-ethanone (10 g, 66 mmol) in DMF (90 mL). The mixture was stirred for 2 hours and then partitioned between 1N HCl and EtOAc. The organic layers were washed with brine, dried over Na2SO4 and concentrated. Purification by flash column chromatography (0% to 20% EtOAc in hexanes) followed by recrystallization gave the title compound as a white solid (8.7 g, 55%). 1H NMR (400 MHz, CDCl3): δ 2.55 (s, 3H), 5.09 (s, 2H), 6.50 (s, 1H), 6.51 (dd, J=9.1, 3.9 Hz, 1H), 7.34-7.43 (m, 5H), 7.64 (d, J=9.1 Hz, 1H), 12.73 (s, 1H).

Workup

  1. custompartitioned between 1N HCl and EtOAc
  2. washThe organic layers were washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customPurification by flash column chromatography (0% to 20% EtOAc in hexanes)
  6. customfollowed by recrystallization

Sources & evidence

ORD record
ord-73b20c14fa3647f6a192bedafaa7f8a5
Source dataset
uspto-grants-2009_01
Patent number
US07473790B2

Reaction notes

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