Nitric Acid → Methyl 3-(4-nitrophenyl)cyclopentanecarboxylate

HRID 1713838Notes

Reaction equation

HRID 1713838 reaction equation
[N+:1]([O-:4])(O)=[O:2].S(=O)(=O)(O)O.[C:10]1([CH:16]2[CH2:20][CH2:19][CH:18]([C:21]([O:23][CH3:24])=[O:22])[CH2:17]2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C(Cl)(Cl)(Cl)Cl>[N+:1]([C:13]1[CH:14]=[CH:15][C:10]([CH:16]2[CH2:20][CH2:19][CH:18]([C:21]([O:23][CH3:24])=[O:22])[CH2:17]2)=[CH:11][CH:12]=1)([O-:4])=[O:2]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 14093250Methyl 3-phenylcyclopentane-1-carboxylate

Product 1

HCID 59464325Methyl 3-(4-nitrophenyl)cyclopentanecarboxylateYield 64%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
7.5 °C

Procedure

A mixture of 65% nitric acid (0.95 mL) and 95% sulphuric acid (1.2 mL) in carbon tetrachloride (2.5 mL) was added dropwise to a solution of methyl 3-phenylcyclopentanecarboxylate (Journal of Organic Chemistry, 1988, 53(17), 4021) (1 g, 4.9 mmol) and the mixture was stirred at 5-10° C. for 2 h. Ice/water (30 mL) was added and the mixture was extracted with DCM (2×50 mL). The extracts were combined, washed with water and dried. The residue was adsorbed onto silica and purified by chromatography eluting with 0-30% EtOAc in hexane to give the title compound (782 mg, 64%) as an oil; 1H NMR δ3.90 (3H, s), 7.94-7.97 (2H, m), 8.03-8.06 (2H, m), 8.09-8.12 (2H, m), 8.33-8.36 (2H, m).

Workup

  1. extractionthe mixture was extracted with DCM (2×50 mL)
  2. washwashed with water
  3. customdried
  4. custompurified by chromatography
  5. washeluting with 0-30% EtOAc in hexane

Sources & evidence

ORD record
ord-d87ddfab269e4de999e0a93585cc1caa
Source dataset
uspto-grants-2010_09
Patent number
US07795283B2

Reaction notes

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