Methanol → HCID 3950390, compound

HRID 1287526Notes

Reaction equation

HRID 1287526 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].[CH3:15][OH:16]>O>[CH3:15][O:16][C:12]1([CH2:4][N+:1]([O-:3])=[O:2])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5](=[O:14])[O:13]1

Participants

4

Reactant 2

HCID 887MethanolHCID 772421H-Indene-1,3(2H)-dione, 2-nitro-

Product 1

HCID 3950390HCID 3950390, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2-nitroindane-1,3-dione (22.3g., 0.117 moles) and methanol (100 ml) was heated under reflux for 4 hours, cooled, poured into water (1 liter), allowed to stand overnight then filtered. The solid was extracted with 5% sodium bicarbonate solution (200 ml). The insoluble material was filtered off, dried, and recrystallised from ethanol to give the Ψ-ester, 3-methoxy-3-nitromethylphthalide, m.p. 113°-114°. Acidification of the sodium bicarbonate filtrate, filtration and recrystallisation from ethanol gave the α-methyl ester, 2-methoxycarbonyl-ω-nitroacetophenone, m.p. 108°-9°.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 4 hours
  3. temperaturecooled
  4. filtrationthen filtered
  5. extractionThe solid was extracted with 5% sodium bicarbonate solution (200 ml)
  6. filtrationThe insoluble material was filtered off
  7. customdried
  8. customrecrystallised from ethanol

Sources & evidence

ORD record
ord-36ec228077e14b9ba8d29f10c6527974
Source dataset
uspto-grants-1976_10
Patent number
US03984565

Reaction notes

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