Benzyl Chloride → Acetophenone

HRID 597438

Reaction equation

HRID 597438 reaction equation
[CH3:1][C:2]([C:4]1[C:9](O)=[CH:8][C:7](O)=[CH:6][C:5]=1O)=[O:3].C(Cl)C1C=CC=CC=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.[Na+].[Cl-]>[C:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)(=[O:3])[CH3:1]

Participants

6

Reactant 3

HCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 680732',4',6'-Trihydroxyacetophenone

Product 1

HCID 7410Acetophenone

Reagents, catalysts & solvents 2

HCID 5234Sodium ChlorideSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 1.68g of phloroacetophenone and 12.7 g of benzyl chloride in 20 ml of DMF is added 5.53 g of anhydrous K2CO3. The mixture is stirred for 16 hours at 65° under argon. The mixture is diluted with 100 ml of 5% NaCl and extracted with ethyl acetate (2 × 50 ml). The extracts are washed with 5% NaCl and 2% NaOH, dried over MgSO4 and concentrated to a red oil which is purified on a dry 250 g silica gel columning CCl4 as eluent. This yields 2,4,6-tribenzyloxyacetophenone as a yellow oil.

Workup

  1. extractionextracted with ethyl acetate (2 × 50 ml)
  2. washThe extracts are washed with 5% NaCl and 2% NaOH
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated to a red oil which
  5. customis purified on a dry 250 g silica gel

Sources & evidence

ORD record
ord-37b556da94d4454a8425a0e130f35973
Source dataset
uspto-grants-1977_03
Patent number
US04013801

Linked notes

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