Acetone → 1-(3,4-Dichlorophenyl)-2-phenylethanone

HRID 1607210Notes

Reaction equation

HRID 1607210 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[OH:10])[CH:5]=[CH:6][C:7]=1[Cl:8].CC(C)=O.S(=O)(=O)(O)O>O>[CH2:11]([C:9]([C:4]1[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=1)=[O:10])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 180AcetoneHCID 1118Sulfuric AcidHCID 198527923,4-Dichlorophenyl benzyl carbinol

Product 1

HCID 27581451-(3,4-Dichlorophenyl)-2-phenylethanone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

In a 500 ml round bottomed flask was placed 75 g of crude 3,4-dichlorophenyl benzyl carbinol and 300 ml of acetone. The reaction mixture was cooled to 0° C. and a solution of 20 g of chromic anhydride and 17.25 ml of concentrated sulfuric acid in 60 ml of water was added at a rate to keep the internal temperature below 5° C. After stirring an additional 15 minutes, the reaction was quenched with 10 ml of isopropanol and partitioned between ethyl ether and water. The organic layer was washed with brine, dried, and concentrated. The resulting crude ketone was crystallized from hexane yielding 51 g of 3,4-dichlorophenyl benzyl ketone. NMR data was consistent with the structure.

Workup

  1. customIn a 500 ml round bottomed flask was placed
  2. customthe internal temperature below 5° C
  3. customthe reaction was quenched with 10 ml of isopropanol
  4. custompartitioned between ethyl ether and water
  5. washThe organic layer was washed with brine
  6. customdried
  7. concentrationconcentrated
  8. customThe resulting crude ketone was crystallized from hexane yielding 51 g of 3,4-dichlorophenyl benzyl ketone

Sources & evidence

ORD record
ord-f1ab14c89bb244719691a29507a292ca
Source dataset
uspto-grants-1989_09
Patent number
US04863947

Reaction notes

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