Butyryl chloride → 4'-Methylbutyrophenone

HRID 897924Notes

Reaction equation

HRID 897924 reaction equation
B(O)(O)[C:2]1[CH:3]=[CH:4][C:5]([CH3:8])=[CH:6][CH:7]=1.[C:11](=[O:14])([O-])[O-].[Cs+].[Cs+].[C:17](Cl)(=O)[CH2:18][CH2:19]C>C1(C)C=CC=CC=1.CCOCC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:8][C:5]1[CH:4]=[CH:3][C:2]([C:11](=[O:14])[CH2:17][CH2:18][CH3:19])=[CH:7][CH:6]=1

Participants

7

Reactant 3

HCID 8855Butyryl chlorideHCID 10796Cesium carbonateHCID 79799Tolylboronic acid

Product 1

HCID 778114'-MethylbutyrophenoneYield 75.2%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
100 °C

Procedure

p-Tolylboronic acid (0.150 g, 1.10 mmol), tetrakis(triphenylphosphine)palladium(0) (0.064 g, 0.055 mmol), and cesium carbonate (1.80 g, 5.52 mmol) were suspended in toluene (25 mL). The reaction mixture was purged under a vigorous flow of nitrogen for 15 minutes. Butyryl chloride (0.344 mL, 3.31 mmol) was added, and the reaction mixture was heated at 100° C. under an atmosphere of nitrogen for 24 h. The reaction mixture was cooled to ambient temperature and diluted with ether (100 mL). The organic layer was extracted sequentially with water (10 mL), aqueous sodium bicarbonate (10 mL), and aqueous sodium chloride (10 mL). The organic layer was dried (magnesium sulfate), filtered, and concentrated. Purification of the residue by flash column chromatography (7.5% ether/petroleum ether) afforded 1-(4-methylphenyl)-1-butanone as a colorless oil (0.134 g, 0.827 mmol): 1H NMR (CDCl3, 400 MHz) δ 7.86 (d, 2H), 7.25 (d, 2H), 2.92 (t, 2H), 2.41 (s, 3H), 1.76 (sx, 2H), 1.00 (t, 3H).

Workup

  1. customThe reaction mixture was purged under a vigorous flow of nitrogen for 15 minutes
  2. temperatureThe reaction mixture was cooled to ambient temperature
  3. extractionThe organic layer was extracted sequentially with water (10 mL), aqueous sodium bicarbonate (10 mL), and aqueous sodium chloride (10 mL)
  4. dry with materialThe organic layer was dried (magnesium sulfate)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification of the residue by flash column chromatography (7.5% ether/petroleum ether)

Sources & evidence

ORD record
ord-fb611cfad1204fce92670c8a728bdac2
Source dataset
uspto-grants-2005_07
Patent number
US06921763B2

Reaction notes

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