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

HRID 2097284Notes

Reaction equation

HRID 2097284 reaction equation
C(=O)([O-])[O-].[K+].[K+].[OH:7][C:8]1[CH:13]=[C:12]([OH:14])[CH:11]=[CH:10][C:9]=1[C:15](=[O:17])[CH3:16].[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C(#N)C>[CH2:18]([O:7][C:8]1[CH:13]=[C:12]([O:14][CH2:15][C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:8]=2)[CH:11]=[CH:10][C:9]=1[C:15](=[O:17])[CH3:16])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

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

Product 1

HCID 3194691-(2,4-Bis(benzyloxy)phenyl)ethanone

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Potassium carbonate (2.5 eq) was added to a solution of 2′,4′-dihydroxyacetophenone (1 eq) in acetonitrile (400 mL), and the suspension stirred at room temperature. Benzyl bromide (2.5 eq) was added drop wise over 10 minutes and the mixture heated at reflux for 18 hours. The mixture was cooled and evaporated in vacuo to give slurry. The slurry was partitioned between water and ethyl acetate, and the layers were separated. The aqueous layer was further extracted with dichloromethane and the organic extracts were combined, dried (MgSO4) and evaporated in vacuo. The product was triturated with hexane, filtered and washed with cold hexane and dried in vacuo at 45° C. to give 1-(2,4-Bis-benzyloxy-phenyl)-ethanone as a white powder.

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux for 18 hours
  3. temperatureThe mixture was cooled
  4. customevaporated in vacuo
  5. customto give slurry
  6. customThe slurry was partitioned between water and ethyl acetate
  7. customthe layers were separated
  8. extractionThe aqueous layer was further extracted with dichloromethane
  9. dry with materialdried (MgSO4)
  10. customevaporated in vacuo
  11. customThe product was triturated with hexane
  12. filtrationfiltered
  13. washwashed with cold hexane
  14. customdried in vacuo at 45° C.

Sources & evidence

ORD record
ord-597bbe713a3046a38107f18d889f3da1
Source dataset
uspto-grants-2013_05
Patent number
US08450310B2

Reaction notes

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