Benzoyl chloride → 2-Butanone, 4-(benzoyloxy)-

HRID 917397Notes

Reaction equation

HRID 917397 reaction equation
[O:1]=[C:2]([CH3:6])[CH2:3][CH2:4][OH:5].[C:7](Cl)(=[O:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C(N(CC)CC)C>O1CCCC1>[O:1]=[C:2]([CH3:6])[CH2:3][CH2:4][O:5][C:7](=[O:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 1115094-Hydroxy-2-Butanone

Product 1

HCID 108994682-Butanone, 4-(benzoyloxy)-Yield 96.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 400 ml of tetrahydrofuran in a reactor, 15.0 g (0.17 mol) of 3-oxo-1-butanol and 26.3 g (0.19 mol) of benzoyl chloride were dissolved, followed by drop-wise adding 20.6 g (0.20 mol) of triethylamine under ice-cooling. After the end of drop-wise addition, the reaction liquid was stirred at room temperature for 3 hours. Hydrochloric acid salt of triethylamine was filtered, followed by adding water to the filtrate and extracting with ethyl acetate. The organic layer was washed with water, a saturated aqueous solution of sodium carbonate, water and a saturated saline solution in this order, followed by drying over anhydrous magnesium sulfate and concentrating under reduced pressure. The residue was purified with silica gel column chromatography (ethyl acetate:hexane=1:5 to 1:3) to obtain 31.5 g (yield: 96%) of 3-oxobutylbenzoate.

Workup

  1. temperaturecooling
  2. additionAfter the end of drop-wise addition
  3. customthe reaction liquid
  4. filtrationHydrochloric acid salt of triethylamine was filtered
  5. additionby adding water to the filtrate
  6. extractionextracting with ethyl acetate
  7. washThe organic layer was washed with water
  8. dry with materialby drying over anhydrous magnesium sulfate
  9. concentrationconcentrating under reduced pressure
  10. customThe residue was purified with silica gel column chromatography (ethyl acetate:hexane=1:5 to 1:3)

Sources & evidence

ORD record
ord-fa5efccac5544ebd84eabf9eb14ec243
Source dataset
uspto-grants-2007_09
Patent number
US07273878B2

Reaction notes

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