Isobutyric Acid → 2-Isobutyryl-5-methylfuran

HRID 1194131Notes

Reaction equation

HRID 1194131 reaction equation
[C:1]([OH:6])(=O)[CH:2]([CH3:4])[CH3:3].[CH3:7][C:8]1[O:9][CH:10]=[CH:11][CH:12]=1.ClC(Cl)C(OC(=O)C(Cl)Cl)=O>C1(C)C=CC=CC=1>[C:1]([C:10]1[O:9][C:8]([CH3:7])=[CH:12][CH:11]=1)(=[O:6])[CH:2]([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 6590Isobutyric AcidHCID 107972-MethylfuranHCID 77772Acetic acid, 2,2-dichloro-, 1,1'-anhydride

Product 1

HCID 110625642-Isobutyryl-5-methylfuranYield 88.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
50 °C

Procedure

In 50 ml of toluene were dissolved 4.41 g (0.05 mole) of isobutyric acid, 5.34 g (0.065 mole) of 2-methylfuran and 14.39 g (0.06 mole) of dichloroacetic anhydride. To the resulting solution was added 0.71 g of boron trifluoride-diethyl ether complex and the resulting mixture was then stirred at 50° C. for 3 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 6.74 g of 2-isobutyryl-5-methylfuran.

Workup

  1. additionTo the resulting solution was added 0.71 g of boron trifluoride-diethyl ether complex
  2. customAfter completion of the reaction
  3. temperaturethe reaction solution was cooled
  4. washwashed successively with 5% aqueous sodium carbonate solution and water
  5. concentrationThe organic layer was concentrated under reduced pressure
  6. customthe resulting concentrated residue was then purified by silica gel-
  7. additionfilled column chromatography

Sources & evidence

ORD record
ord-7329d06353ce42bdb339d893fe785303
Source dataset
uspto-grants-1989_03
Patent number
US04812585

Reaction notes

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