Nitric Acid → Methyl 3-(4-nitrophenyl)cyclobutane-1-carboxylate

HRID 2420141Notes

Reaction equation

HRID 2420141 reaction equation
[N+:1]([O-:4])(O)=[O:2].[C:5]1([CH:11]2[CH2:14][CH:13]([C:15]([O:17][CH3:18])=[O:16])[CH2:12]2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>C(OC(=O)C)(=O)C.C(O)(=O)C>[N+:1]([C:8]1[CH:9]=[CH:10][C:5]([CH:11]2[CH2:12][CH:13]([C:15]([O:17][CH3:18])=[O:16])[CH2:14]2)=[CH:6][CH:7]=1)([O-:4])=[O:2]

Participants

5

Reactant 2

HCID 944Nitric AcidHCID 20313170HCID 20313170, compound

Product 1

HCID 20313166Methyl 3-(4-nitrophenyl)cyclobutane-1-carboxylate

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 7918Acetic AnhydrideSolvent

Procedure

Fuming nitric acid (0.54ml.) was added dropwise to a stirred solution of methyl 3-phenylcyclobutanecarboxylate (950mg.) in acetic anhydride (5ml.) and glacial acetic acid (0.25ml.) at -5° C. The reaction mixture was set aside overnight at room temperature then poured onto ice and extracted with ethyl acetate (3 × 20ml.). The ethyl acetate solution was dried over magnesium sulphate and evaporated under reduced pressure. Chromatography of the residue on a column of "Florisil" (25g.), eluting with toluene, gave methyl 3-(4-nitrophenyl)cyclobutanecarboxylate as a pale yellow oil. The n.m.r. spectrum in deuteriochloroform showed the following characteristic signals (δ values):

Workup

  1. additionthen poured onto ice
  2. extractionextracted with ethyl acetate (3 × 20ml.)
  3. dry with materialThe ethyl acetate solution was dried over magnesium sulphate
  4. customevaporated under reduced pressure
  5. washChromatography of the residue on a column of "Florisil" (25g.), eluting with toluene

Sources & evidence

ORD record
ord-0bf59d7df8494a279445f49b3ba30fff
Source dataset
uspto-grants-1978_08
Patent number
US04109015

Reaction notes

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