Benzene → Cyclobutyl phenyl ketone

HRID 359542Notes

Reaction equation

HRID 359542 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[CH:5]1([C:9](Cl)=[O:10])[CH2:8][CH2:7][CH2:6]1.[CH:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>>[CH:5]1([C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:10])[CH2:8][CH2:7][CH2:6]1

Participants

4

Reactant 3

HCID 241BenzeneHCID 78705Cyclobutanecarbonyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 79414Cyclobutyl phenyl ketone

Procedure

In a 5-L round bottomed flask equipped with an overhead stirrer and a pressure equalizing additional funnel was placed 1500 mL of benzene and 1150 g (8.65 mole) of anhydrous aluminum chloride. The reaction vessel was cooled in an ice-salt bath. To this mixture was added very carefully over a 1.5 hour period 920 g (7.7 mole) of cyclobutanecarbonyl chloride. Following the addition, the cooling bath was removed and the mixture allowed to warm to room temperature overnight and cautiously poured onto ice. The phases were separated and the aqueous layer extracted three times with ethyl acetate. The organic layers were combined washed three times with saturated sodium bicarbonate three times with water, and once with brine. The solution was dried over anhydrous magnesium sulfate and the solvent removed under reduced pressure. The residue was distilled to give 1126 g of phenyl cyclobutyl ketone, bp 97°-102° C. at 0.1 mm Hg. NMR (CDCl3) 1.8-2.6 (m, 6 H), 4.0 (q, 1 H), 7.4-7.6 (m, 3 H), 7.8-8.0 (m, 2 H); IR (neat film) 2950, 1675, 1450, 1350, 1225, 960, and 700 cm-1.

Workup

  1. customIn a 5-L round bottomed flask equipped with an overhead stirrer
  2. temperatureThe reaction vessel was cooled in an ice-salt bath
  3. additionthe addition
  4. customthe cooling bath was removed
  5. additioncautiously poured onto ice
  6. customThe phases were separated
  7. extractionthe aqueous layer extracted three times with ethyl acetate
  8. washThe organic layers were combined washed three times with saturated sodium bicarbonate three times with water
  9. dry with materialThe solution was dried over anhydrous magnesium sulfate
  10. customthe solvent removed under reduced pressure
  11. distillationThe residue was distilled

Sources & evidence

ORD record
ord-ad2e5fd614e24712832361115fe1863c
Source dataset
uspto-grants-1991_03
Patent number
US05001160

Reaction notes

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