Propionic Acid → 1-(2-Furyl)propan-1-one

HRID 1194127Notes

Reaction equation

HRID 1194127 reaction equation
[C:1]([OH:5])(=O)[CH2:2][CH3:3].ClCC(OC(=O)CCl)=O.[CH3:15][C:16]1[O:17]C=[CH:19][CH:20]=1>C1(C)C=CC=CC=1>[C:16]([C:15]1[O:5][CH:1]=[CH:2][CH:3]=1)(=[O:17])[CH2:20][CH3:19]

Participants

5

Conditions

Temperature
50 °C

Procedure

In 50 ml of toluene were dissolved 3.7 g (0.05 mole) of propionic acid and 10.26 g (0.06 mole) of monochloroacetic anhydride. To the resulting solution were added 5.36 g (0.065 mole) of 2-methylfuran and 0.71 g of boron trifluoride-diethyl ether complex and the resulting mixture was then stirred at 50° C. for 7 hours. After completion of the reaction, the reaction solution was cooled and washed successively with 5% aqueous sodium carbonate solution and water. The organic layer was concentrated under reduced pressure and the resulting concentrated residue was then purified by silica gel-filled column chromatography to obtain 2.96 g of 2-propionylfuran.

Workup

  1. customAfter completion of the reaction
  2. temperaturethe reaction solution was cooled
  3. washwashed successively with 5% aqueous sodium carbonate solution and water
  4. concentrationThe organic layer was concentrated under reduced pressure
  5. customthe resulting concentrated residue was then purified by silica gel-
  6. additionfilled column chromatography

Sources & evidence

ORD record
ord-2585bff7b5a548d4aeb6da610803c30e
Source dataset
uspto-grants-1989_03
Patent number
US04812585

Reaction notes

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