Hydrochloric Acid → 2-Phenylacetophenone

HRID 444289Notes

Reaction equation

HRID 444289 reaction equation
[C:1]1([C:7]([CH:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)O)=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Sn].Cl>O>[C:1]1([C:7]([CH2:9][C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8400BenzoinHCID 5352426Tin atom

Product 1

HCID 99482-Phenylacetophenone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The benzoin (0.075 mole) was dissolved in 80 ml. of alcohol and 20 g. of tin (20 mesh) was added. The mixture was gently heated and a solution containing 28 ml. of concentrated hydrochloric acid, 0.8 g. of anhydrous cupric sulfate and 0.5 ml. of water was added. The reaction mixture was refluxed until thin layer chromatography no longer detected the presence of starting material. The granular tin was removed by filtration and the filtrate was evaporated to an oil which was diluted with water to 400 ml. and was extracted with chloroform. The organic extract was washed with 5% aqueous sodium carbonate solution (45 ml.×3), with water (45 ml.×2) and with brine; it was dried over anhydrous magnesium sulfate and evaporated to obtain desoxybenzoin.

Workup

  1. temperatureThe mixture was gently heated
  2. additiona solution containing 28 ml
  3. temperatureThe reaction mixture was refluxed until thin layer chromatography
  4. customThe granular tin was removed by filtration
  5. customthe filtrate was evaporated to an oil which
  6. additionwas diluted with water to 400 ml
  7. extractionand was extracted with chloroform
  8. extractionThe organic extract
  9. washwas washed with 5% aqueous sodium carbonate solution (45 ml.×3), with water (45 ml.×2) and with brine
  10. dry with materialit was dried over anhydrous magnesium sulfate
  11. customevaporated

Sources & evidence

ORD record
ord-6f2fe239ea9845f5b573e9d42e4952c3
Source dataset
uspto-grants-1981_04
Patent number
US04263311

Reaction notes

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