4-Methylbenzophenone → Ethyl acetate hexane

HRID 2081188Notes

Reaction equation

HRID 2081188 reaction equation
C[C:2]1[CH:15]=[CH:14][C:5]([C:6]([C:8]2C=CC=CC=2)=[O:7])=[CH:4][CH:3]=1.BrN1[C:21](=[O:22])[CH2:20]CC1=O>C(Cl)(Cl)(Cl)Cl>[C:21]([O:7][CH2:6][CH3:8])(=[O:22])[CH3:20].[CH3:14][CH2:15][CH2:2][CH2:3][CH2:4][CH3:5]

Participants

4

Reactant 2

HCID 86524-MethylbenzophenoneHCID 67184N-bromobutanimide

Product 1

HCID 21226206Ethyl acetate hexaneYield 129%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

1 To a solution of 4-methylbenzophenone (3.0 g, 15.3 mmol) in 60 ml CCl4 was added N-bromosuccinimide (3.0 g, 1.1 eq) and AlBN (30 mg). The solution was refluxed for 4.5 h, then cooled to room temperature. The succinimide were removed by filtration, and the filtrate was concentrated to dryness. Recrystallization required large amounts of solvent and chromatography appeared a better alternative. The residue was chromatographed on silica gel eluting with 5% Ethyl Acetate/Hexane (3.44 g; 82% yield).

Workup

  1. temperatureThe solution was refluxed for 4.5 h
  2. customThe succinimide were removed by filtration
  3. concentrationthe filtrate was concentrated to dryness
  4. customRecrystallization required large amounts of solvent and chromatography

Sources & evidence

ORD record
ord-368dad565c934343ad7efa1b4103e2f9
Source dataset
uspto-grants-1993_02
Patent number
US05183810

Reaction notes

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