Benzene → HCID 13576940, compound

HRID 544709Notes

Reaction equation

HRID 544709 reaction equation
[C:1]([O-:9])(=[O:8])[C:2]1C=CC=C[CH:3]=1.[NH2+:10]1[CH2:14][CH2:13][CH2:12][CH2:11]1.O.[CH:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>>[CH3:3][CH:2]1[C:17]2[CH:18]=[CH:19][C:20]([N:10]3[CH2:14][CH2:13][CH2:12][CH2:11]3)=[CH:21][C:16]=2[O:9][C:1]1=[O:8]

Participants

4

Reactant 3

HCID 241BenzeneHCID 962WaterHCID 70505146HCID 70505146, compound

Product 1

HCID 13576940HCID 13576940, compound

Procedure

A mixture of 18.2 g (0.1 mole) of 4-methyl-3-(3-oxobutyl)-maleic acid anhydride and 20.3 g (0.105 mole) of pyrrolidinium benzoate in 400 ml of benzene is heated under reflux for 24 hours using a water separator. The benzene is then removed in vacuo and the residue that remains is partitioned between methylene chloride and saturated sodium bicarbonate solution. The crude product remaining after drying and after removal of the methylene chloride is chromatographed over silica gel with petroleum ether/ether. Subsequent recrystallisation from ether. Subsequent recrystallisation from ether/petroleum ether yields 3-methyl-6-(pyrrolidin-1-yl)-benzofuran-2(3H)-one having a melting point of 101°-103° C.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 24 hours
  3. customThe benzene is then removed in vacuo
  4. customthe residue that remains is partitioned between methylene chloride and saturated sodium bicarbonate solution
  5. customafter drying
  6. customafter removal of the methylene chloride
  7. customis chromatographed over silica gel with petroleum ether/ether
  8. customSubsequent recrystallisation from ether
  9. customSubsequent recrystallisation from ether/petroleum ether

Sources & evidence

ORD record
ord-165367b16c854d1bb164eac19e419d2f
Source dataset
uspto-grants-1984_05
Patent number
US04451462

Reaction notes

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