Nitric Acid → Spiro(benzofuran-2(3H),1'-cyclopropan)-3-one, 5-nitro-

HRID 894615Notes

Reaction equation

HRID 894615 reaction equation
[C:1]12([O:7][C:6]3[CH:8]=[CH:9][CH:10]=[CH:11][C:5]=3[C:4]1=[O:12])[CH2:3][CH2:2]2.[N+:13]([O-])([OH:15])=[O:14]>>[N+:13]([C:10]1[CH:9]=[CH:8][C:6]2[O:7][C:1]3([C:4](=[O:12])[C:5]=2[CH:11]=1)[CH2:3][CH2:2]3)([O-:15])=[O:14]

Participants

3

Reactant 2

HCID 944Nitric AcidHCID 3055472Spiro(benzofuran-2(3H),1'-cyclopropan)-3-one

Product 1

HCID 3055474Spiro(benzofuran-2(3H),1'-cyclopropan)-3-one, 5-nitro-

Procedure

Spiro[benzo[b]furan-2(3H), 1'-cyclopropane]-3-one (7.0 g.) was added in small portions to fuming nitric acid (70 ml.) previously cooled to -50° C. to -60° C. After stirring for 20 minutes, the reaction mixture was poured into ice-water and the precipitated crystals were collected by filtration, washed with water and recrystallized from ethanol. By the above procedure there was obtained 5-nitrospiro[benzo[b]furan-2(3H),1'-cyclopropane]-3-one as colorless prisms, m.p. 107°-110° C. Yield 7.3 g. This product was in good agreement with the crystals obtained in Example 18.

Workup

  1. temperaturepreviously cooled to -50° C. to -60° C
  2. filtrationthe precipitated crystals were collected by filtration
  3. washwashed with water
  4. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-9709cb917ec94f368c713a7e43414980
Source dataset
uspto-grants-1981_08
Patent number
US04284644

Reaction notes

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