Hydrochloric Acid → 2-Methylbenzophenone

HRID 1679249

Reaction equation

HRID 1679249 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-].[Al+3].[Cl-].[Cl-].O.Cl.[C:16]1([CH3:22])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>>[CH3:22][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[C:1]([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:8]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 962WaterHCID 1140TolueneHCID 7412Benzoyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 672302-MethylbenzophenoneYield 93%

Procedure

To a mechanically stirred solution of 1000 grams (7.12 moles) of benzoyl chloride in 6000 grams of toluene was added 1000 grams (7.50 moles) of anhydrous aluminum chloride over a 20- 30 minute period. The temperature of the reaction mixture rose to near the boiling point during the addition, and heating at reflux was maintained for three additional hours. After cooling, 1200 milliliters of water were added, slowly at first, followed by 1000 milliliters of concentrated hydrochloric acid. The organic layer was separated, washed twice with hot water and concentrated on a rotary evaporator. Vacuum distillation of the residual oil provided 1300 grams (93% yield) of white, semi-solid methyl benzophenone; (b.p. 180°-200° C., 10- 15 mm Hg; m.p. 50° C.) The infrared spectrum revealed a carbonyl band at 1665 cm -1.

Workup

  1. additionThe temperature of the reaction mixture rose to near the boiling point during the addition
  2. temperatureheating
  3. temperatureat reflux
  4. temperaturewas maintained for three additional hours
  5. temperatureAfter cooling
  6. customThe organic layer was separated
  7. washwashed twice with hot water
  8. concentrationconcentrated on a rotary evaporator
  9. distillationVacuum distillation of the residual oil

Sources & evidence

ORD record
ord-820b8d96fd9b4cbdbea9810f5e54b0f6
Source dataset
uspto-grants-1978_03
Patent number
US04080275

Linked notes

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