Water → Cyclobutyl(4-methylphenyl)methanone

HRID 436926Notes

Reaction equation

HRID 436926 reaction equation
[CH:1]1([C:5](Cl)=[O:6])[CH2:4][CH2:3][CH2:2]1.[Cl-].[Al+3].[Cl-].[Cl-].O.[C:13]1([CH3:19])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>>[C:13]1([CH3:19])[CH:18]=[CH:17][C:16]([C:5]([CH:1]2[CH2:4][CH2:3][CH2:2]2)=[O:6])=[CH:15][CH:14]=1

Participants

5

Reactant 4

HCID 962WaterHCID 1140Toluene2×HCID 78705Cyclobutanecarbonyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 316820Cyclobutyl(4-methylphenyl)methanone

Procedure

Cyclobutylcarbonyl chloride (23.8 g.) in dry toluene (25 ml) was added dropwise during 1 hour to a stirred suspension of anhydrous aluminium chloride (29.4 g) in dry toluene (150 ml). After stirring a further 20 minutes, the mixture was poured into iced water (1 l) and the organic layer was separated, washed with water, dried over magnesium sulphate, filtered and evaporated. The residue was distilled under reduced pressure and the fraction b.p. 79-80°/0.03 mm was collected. On standing the product solidified and the solid had m.p. 32°-34°.

Workup

  1. customthe organic layer was separated
  2. washwashed with water
  3. dry with materialdried over magnesium sulphate
  4. filtrationfiltered
  5. customevaporated
  6. distillationThe residue was distilled under reduced pressure
  7. customthe fraction b.p. 79-80°/0.03 mm was collected

Sources & evidence

ORD record
ord-6f813a29c7da4115a3f02b2b9428c00e
Source dataset
uspto-grants-1977_06
Patent number
US04028404

Reaction notes

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