alpha-Methyl-3-chloro-4-phenylbenzyl alcohol → 4-Acetyl-2-chloro-biphenyl

HRID 1578863Notes

Reaction equation

HRID 1578863 reaction equation
[CH3:1][CH:2]([OH:16])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[C:5]([Cl:15])[CH:4]=1>CC(C)=O.S(=O)(=O)(O)O.[O-2].[O-2].[O-2].[Cr+6]>[Cl:15][C:5]1[CH:4]=[C:3]([C:2](=[O:16])[CH3:1])[CH:8]=[CH:7][C:6]=1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 1

HCID 54396951alpha-Methyl-3-chloro-4-phenylbenzyl alcohol

Product 1

HCID 127880424-Acetyl-2-chloro-biphenyl

Reagents, catalysts & solvents 3

HCID 10219390chromium (VI) trioxideCatalystHCID 180AcetoneSolvent2×HCID 1118Sulfuric AcidSolvent

Procedure

α-methyl-3-chloro-4-phenylbenzyl alcohol, 28.6 g, was dissolved in 36 ml of acetone. To the resulting solution was added dropwise, with cooling and vigorous agitation, a solution of 12 g of chromium trioxide in 42 ml of 35 percent aqueous sulfuric acid. A large volume of acetone then was added; the aqueous layer was separated and washed with acetone. The acetone layer and acetone extracts were combined and dried over anhydrous sodium sulfate. The acetone was evaporated and the residue was distilled in vacuo to give 26.3 g of 3'-chloro-4'-phenylacetophenone, bp 132°-141°C/0.09 mm. The following elemental analysis was obtained:

Workup

  1. additionTo the resulting solution was added dropwise
  2. temperaturewith cooling
  3. customthe aqueous layer was separated
  4. washwashed with acetone
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe acetone was evaporated
  7. distillationthe residue was distilled in vacuo

Sources & evidence

ORD record
ord-68ecea8151d04022a10041264d5d95df
Source dataset
uspto-grants-1976_02
Patent number
US03939278

Reaction notes

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