Nitric Acid → 4-(4-Nitrophenyl)cyclohexanone

HRID 1477481Notes

Reaction equation

HRID 1477481 reaction equation
OS(O)(=O)=O.[C:6]1([CH:12]2[CH2:17][CH2:16][C:15](=[O:18])[CH2:14][CH2:13]2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[N+:19]([O-])([OH:21])=[O:20]>>[N+:19]([C:9]1[CH:10]=[CH:11][C:6]([CH:12]2[CH2:17][CH2:16][C:15](=[O:18])[CH2:14][CH2:13]2)=[CH:7][CH:8]=1)([O-:21])=[O:20]

Participants

4

Reactant 3

HCID 944Nitric Acid2×HCID 1118Sulfuric AcidHCID 786054-Phenylcyclohexanone

Product 1

HCID 212604964-(4-Nitrophenyl)cyclohexanoneYield 10%

Procedure

Concentrated H2SO4 (20 mL) was cooled to 0° C. and treated with 4-phenyl-cyclohexanone (4.22 g, 24.2 mmol), and fuming nitric acid (1.6 mL) was added very carefully dropwise, keeping the temperature of the mixture below 20° C. After the addition of nitric acid was complete, the mixture was warmed to RT and allowed to stir for 5 h. The mixture was poured over ice (200 mL) and extracted with EtOAc (3×150 mL). The combined organic layers were dried over MgSO4 and concentrated in vacuo. Silica gel chromatography with 10% EtOAc-hexane on a 70-g Isolute SPE column (FlashMaster system) afforded the title compound (0.512 g, 10%) as a pale yellow solid. 1H-NMR (CD3OD; 400 MHz): δ 8.20 (d, 2H, J=8.8 Hz), 7.42 (d, 2H, J=8.8 Hz), 3.16 (tt, 1H, J=12.0, 4.0 Hz), 2.58-2.51 (m, 4H), 2.31-2.21 (m, 2H), 2.05-1.91 (m, 2H).

Workup

  1. additionwas added very carefully dropwise
  2. customthe temperature of the mixture below 20° C
  3. extractionextracted with EtOAc (3×150 mL)
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d5d9b2ff4aeb4aad8b9d58003f23d6bb
Source dataset
uspto-grants-2016_08
Patent number
US09403804B2

Reaction notes

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