Hydrochloric Acid → 2-Methylbenzophenone

HRID 2049903Notes

Reaction equation

HRID 2049903 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 benzoylchloride 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 by simple distillation. 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°-55° C.). The infrared spectrum revealed a carbonyl band at 1660 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 by simple distillation
  9. distillationVacuum distillation of the residual oil

Sources & evidence

ORD record
ord-4d8b6d33db264b8c9b33d73fddc645ae
Source dataset
uspto-grants-1980_04
Patent number
US04199420

Reaction notes

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