Ethanol → HCID 21509235, compound

HRID 1287527Notes

Reaction equation

HRID 1287527 reaction equation
[N+:1]([CH:4]1[C:12](=[O:13])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]1=[O:14])([O-:3])=[O:2].O.[CH2:16]([OH:18])[CH3:17]>>[CH2:16]([O:18][C:12]([CH:4]([N+:1]([O-:3])=[O:2])[C:5]([C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1)=[O:14])=[O:13])[CH3:17]

Participants

4

Reactant 3

HCID 702EthanolHCID 962WaterHCID 772421H-Indene-1,3(2H)-dione, 2-nitro-

Product 1

HCID 21509235HCID 21509235, compound

Procedure

2-Nitroindane-1,3-dione (20.5g; 0.107 moles) in ethanol (100 ml) was heated under reflux for 4 hours, cooled, poured into water (1 liter), allowed to stand overnight and filtered. The solid was extracted with 5% sodium bicarbonate solution (3 × 100 ml) and filtered. The insoluble solid was predominantly the Ψ-ethyl ester, 3-ethoxy-3-nitromethylphthalide, contaminated with some α-ethyl ester. Acidification of the combined sodium bicarbonate filtrates, filtration and recrystallisation from ethanol gave the α-ethyl ester, 2-ethoxycarbonyl-ω-nitroacetophenone, m.p. 81°.

Workup

  1. temperatureunder reflux for 4 hours
  2. temperaturecooled
  3. filtrationfiltered
  4. extractionThe solid was extracted with 5% sodium bicarbonate solution (3 × 100 ml)
  5. filtrationfiltered
  6. filtrationAcidification of the combined sodium bicarbonate filtrates, filtration and recrystallisation from ethanol

Sources & evidence

ORD record
ord-3bbff8c95db54a70bff86d25aa2bea0c
Source dataset
uspto-grants-1976_10
Patent number
US03984565

Reaction notes

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