Phenylacetyl chloride → 2-Phenylacetophenone

HRID 1382502Notes

Reaction equation

HRID 1382502 reaction equation
[CH2:1]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[Cl-].[Al+3].[Cl-].[Cl-].C1(CC(Cl)=[O:27])C=CC=CC=1>C(=S)=S>[C:9]1([C:1]([CH2:2][C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)=[O:27])[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 7679Phenylacetyl chlorideHCID 16607OctylbenzeneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 99482-PhenylacetophenoneYield 156.3%

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent2×

Procedure

57.0 g (0.30 mole) of n-octylbenzene are dissolved in 500 ml of carbon disulfide, 45.0 g (0.34 mole) of aluminum chloride are added at 0° C., and a solution of 46.4 g (0.30 mole) of phenylacetyl chloride and 50 ml of carbon disulfide are added dropwise at from 0° to 5° C., while stirring. The reaction mixture is stirred for a further 2 hours at from 0° to 5° C. and then for 15 hours without being cooled, after which it is poured carefully onto 1 l of semiconcentrated ice-cold hydrochloric acid. The phases are separated, the organic phase is extracted by shaking with 300 ml of water, the aqueous phase is extracted with three times 300 ml of methylene chloride, and the combined organic phases are dried over sodium sulfate. The solution is filtered and the solvent is distilled off to give 92 g (=100% of theory) of deoxybenzoin as a colorless crystalline mass, which is shown by thin layer chromatography (silica gel/CH2Cl2 : R≈0.95; toluene: R≈0.61) to be sufficiently pure for the subsequent bromination.

Workup

  1. stirringThe reaction mixture is stirred for a further 2 hours at from 0° to 5° C.
  2. temperaturefor 15 hours without being cooled
  3. customThe phases are separated
  4. extractionthe organic phase is extracted
  5. stirringby shaking with 300 ml of water
  6. extractionthe aqueous phase is extracted with three times 300 ml of methylene chloride
  7. dry with materialthe combined organic phases are dried over sodium sulfate
  8. filtrationThe solution is filtered
  9. distillationthe solvent is distilled off

Sources & evidence

ORD record
ord-7c939213665b41e38e1b83b7c4a834ce
Source dataset
uspto-grants-1989_02
Patent number
US04806664

Reaction notes

Loading…