Toluene → HCID 14473416, compound

HRID 1194128Notes

Reaction equation

HRID 1194128 reaction equation
C(O)(=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].Cl[CH2:11][C:12]([O:14][C:15](=O)[CH2:16]Cl)=O.CC1[O:21]C=CC=1.[C:25]1([CH3:31])C=CC=CC=1>>[C:11]([C:12]1[O:14][C:15]([CH3:16])=[CH:25][CH:31]=1)(=[O:21])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH3:2]

Participants

5

Reactant 4

HCID 1140TolueneHCID 8094Heptanoic AcidHCID 107972-MethylfuranHCID 10946Chloroacetic anhydride

Product 1

HCID 14473416HCID 14473416, compoundYield 69.6%

Conditions

Temperature
50 °C

Procedure

In 50 ml of toluene were dissolved 6.51 g (0.05 mole) of heptanoic acid and 10.26 g (0.06 mole) of monochloroacetic anhydride. To the resulting solution were added 5.34 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 5.5 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 6.27 g of 2-heptanoyl-5-methylfuran.

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-a1cf163bbc6e4f52987cfb7f065f7180
Source dataset
uspto-grants-1989_03
Patent number
US04812585

Reaction notes

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