Nitric Acid → HCID 12925989, compound

HRID 894616Notes

Reaction equation

HRID 894616 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:12](=[O:13])[C:9]3([CH2:11][CH2:10]3)[O:8][C:7]=2[CH:14]=1.C(OC(=O)C)(=O)C.[N+:22]([O-])([OH:24])=[O:23]>C(O)(=O)C>[CH3:1][O:2][C:3]1[C:4]([N+:22]([O-:24])=[O:23])=[CH:5][C:6]2[C:12](=[O:13])[C:9]3([CH2:10][CH2:11]3)[O:8][C:7]=2[CH:14]=1

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 7918Acetic AnhydrideHCID 12783852HCID 12783852, compound

Product 1

HCID 12925989HCID 12925989, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

5.4 g. of 6-Methoxyspiro[benzo[b]furan-2(3H),1'-cyclopropane]-3-one was dissolved in a mixture of 25 ml. of acetic anhydride and 7 ml. of glacial acetic acid. While keeping the reaction temperature at 10°-15° C., 3 ml. of fuming nitric acid (d=1.52) was added dropwise to the mixture. After stirring for 30 minutes, the reaction mixture was poured into ice-water. The resulting precipitates were collected by filtration, washed with water and recrystallized from ethanol. By the above procedure, there was obtained 6-methoxy-5-nitrospiro[benzo[b]furan-2(3H), 1'-cyclopropane]-3-one as pale yellow prisms melting at 160°-163° C. Yield: 4.5 g.

Workup

  1. customat 10°-15° C.
  2. customThe resulting precipitates
  3. filtrationwere collected by filtration
  4. washwashed with water
  5. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-d612cdfa72dd4f0abef7f1459e5df258
Source dataset
uspto-grants-1981_08
Patent number
US04284644

Reaction notes

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