Water → HCID 24757165, compound

HRID 2388376Notes

Reaction equation

HRID 2388376 reaction equation
[C:1]1(=[N:7][OH:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[N+:9]([C:12]1[CH:20]=[CH:19][C:15]([C:16](O)=[O:17])=[CH:14][CH:13]=1)([O-:11])=[O:10].O>C(Cl)Cl>[N:7]([C:1]1([O:17][CH2:16][C:15]2[CH:14]=[CH:13][C:12]([N+:9]([O-:11])=[O:10])=[CH:20][CH:19]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)=[O:8]

Participants

5

Reactant 3

HCID 962WaterHCID 61084-Nitrobenzoic AcidHCID 7517Cyclohexanone Oxime

Product 1

HCID 24757165HCID 24757165, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of cyclohexanone oxime (2.66 g, 23.51 mmol) in methylene chloride (50 mL) was added dropwise with stirring to a solution of LTA (10.42 g, 23.51 mmol) and 4-nitrobenzoic acid (39.29 g, 235.1 mmol) in methylene chloride (300 mL) at 0° C. A blue color gradually appeared with the addition of the oxime. After 1 h at 0° C., the reaction mixture was warmed to room temperature. After 3 h at room temperature, water (50 mL) was added and the organic layer was extracted with water (2×50 mL) and 3% sodium bicarbonate solution (2×50 mL). The organic layer was dried over Na2SO4, the solvent evaporated and the residue was recrystallized in diethyl ether/petroleum ether (1:1) in a −5° C. freezer to give 1-Nitroso-1-para-nitrobenzoxycyclohexane as bright blue crystals (20-25% yield): Rf 0.55 (pentane/ethyl acetate=20:1); 1H NMR (300 MHz, Benzene-d6) δ 1.17-2.04 (m, 10H), 7.38-7.98 (d, 4H); 13C NMR (300 MHz, Benzene-d6) δ 22.1 (2CH2), 25.0 (CH2), 29.7 (2CH2), 123.8 (2Ph-CH), 125.3 (O—C—N), 131.1 (2Ph-CH), 135.3 (Ph-C), 151.1 (Ph-C), 162.6 (C═O).

Workup

  1. waitAfter 3 h at room temperature
  2. extractionthe organic layer was extracted with water (2×50 mL) and 3% sodium bicarbonate solution (2×50 mL)
  3. dry with materialThe organic layer was dried over Na2SO4
  4. customthe solvent evaporated
  5. customthe residue was recrystallized in diethyl ether/petroleum ether (1:1) in a −5° C. freezer

Sources & evidence

ORD record
ord-b8c93f059ecc455da9f6f6e8834cf80b
Source dataset
uspto-grants-2012_09
Patent number
US08269034B2

Reaction notes

Loading…