Nitric Acid → HCID 53999933, compound

HRID 326305Notes

Reaction equation

HRID 326305 reaction equation
[CH3:1][O:2][C:3]1[C:8]2[C:9](=[O:18])[CH2:10][C:11]3([O:17][C:7]=2[CH:6]=[C:5]([O:19][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH:4]=1)[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]3.[N+:26]([O-])([OH:28])=[O:27]>>[CH3:1][O:2][C:3]1[C:8]2[C:9](=[O:18])[CH2:10][C:11]3([O:17][C:7]=2[C:6]([N+:26]([O-:28])=[O:27])=[C:5]([O:19][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH:4]=1)[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]3

Participants

3

Reactant 2

HCID 944Nitric AcidHCID 9863129HCID 9863129, compound

Product 1

HCID 53999933HCID 53999933, compoundYield 74.2%

Procedure

Ethyl 2-{(5-methoxy-3,4-dihydro-4-oxospiro[2H-1-benzopyran-2,1'-cyclohexan]-7-yl) oxy}acetate prepared in Preparation 49) (1.3 g, 3.92 mmol) is added by portions to fuming nitric acid (d=1.50, 10 ml) at -60° C. with stirring. After one hour stirring at -60° to -40° C., the reaction mixture is poured into ice-cold water. The mixture is extracted with diethyl ether. The ether layer is separated, washed with water and then aqueous sodium bicarbonate, dried and concentrated. The residue is washed with diethyl ether. Recrystallization from a mixture of ethyl acetate and hexane gives the title compounds as a crystalline solid (1.05 g, yield 74.2%, m.p.=142°-143° C.).

Workup

  1. stirringAfter one hour stirring at -60° to -40° C.
  2. additionthe reaction mixture is poured into ice-cold water
  3. extractionThe mixture is extracted with diethyl ether
  4. customThe ether layer is separated
  5. washwashed with water
  6. dry with materialaqueous sodium bicarbonate, dried
  7. concentrationconcentrated
  8. washThe residue is washed with diethyl ether
  9. customRecrystallization
  10. additionfrom a mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-d60fc5fb22a141cbbe49340f4bc07062
Source dataset
uspto-grants-1993_12
Patent number
US05268386

Reaction notes

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