Nitric Acid → HCID 12925978, compound

HRID 894614Notes

Reaction equation

HRID 894614 reaction equation
[O:1]1[CH2:5][CH2:4][C:3]2([O:9][C:8]3[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=3[C:6]2=[O:14])[C:2]1=[O:15].S(=O)(=O)(O)O.[N+:21]([O-])([OH:23])=[O:22]>>[N+:21]([C:12]1[CH:11]=[CH:10][C:8]2[O:9][C:3]3([C:6](=[O:14])[C:7]=2[CH:13]=1)[CH2:4][CH2:5][O:1][C:2]3=[O:15])([O-:23])=[O:22]

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric Acid2×HCID 12925964HCID 12925964, compound

Product 1

HCID 12925978HCID 12925978, compound

Procedure

To a solution of 0.408 g. of 4',5'-dihydrospiro[benzo[b]furan-2(3H), 3'(2'H)-furan]-2',3-dione in 3 ml. of concentrated sulfuric acid was added a mixture of 0.35 ml. of nitric acid (d=1.42) and 0.36 ml. of concentrated sulfuric acid, dropwise under ice-cooling, and the mixture was stirred for 2 hours. The reaction mixture was poured into ice-water and the precipitated crystals were collected by filtration, washed with water, dried and recrystallized from ethyl acetate. By the above procedure there was obtained colorless needles of 4',5'-dihydro-5-nitrospiro[benzo[b]furan-2(3H),3'(2'H)-furan]-2',3-dione. m.p. 199°-200° C.

Workup

  1. additiona mixture of 0.35 ml
  2. filtrationthe precipitated crystals were collected by filtration
  3. washwashed with water
  4. customdried
  5. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-344e52eef7834821b813dc9cac39ae54
Source dataset
uspto-grants-1981_08
Patent number
US04284644

Reaction notes

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