Nitric Acid → HCID 178525695, compound

HRID 1713828Notes

Reaction equation

HRID 1713828 reaction equation
S(=O)(=O)(O)O.[N+:6]([O-:9])(O)=[O:7].[C:10]1([C@H:16]2[CH2:21][CH2:20][C@H:19]([C:22]([OH:24])=[O:23])[CH2:18][CH2:17]2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>[N+](C1C=CC=CC=1)([O-])=O>[N+:6]([C:13]1[CH:14]=[CH:15][C:10]([C@H:16]2[CH2:17][CH2:18][C@H:19]([C:22]([OH:24])=[O:23])[CH2:20][CH2:21]2)=[CH:11][CH:12]=1)([O-:9])=[O:7]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 178525692HCID 178525692, compound

Product 1

HCID 178525695HCID 178525695, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 7416NitrobenzeneSolvent

Procedure

A mixture of concentrated sulphuric acid (1.5 mL) and concentrated nitric acid (0.9 mL) was added dropwise to a vigorously stirred solution of trans-4-phenylcyclohexanecarboxylic acid (1.7 g. 8.3 mmol) in nitrobenzene (4 mL) at 5° C. The reaction mixture was warmed to room temperature and stirred for 2.5 h and then poured onto ice. The aqueous mixture was extracted with DCM and the organic layer was concentrated in vacuo to leave a yellow oil, which crystallised to a white solid upon standing. The solid was triturated with toluene and filtered to give the title compound (600 mg, 60%) as a solid; 1H NMR δ 1.4-1.6 (4H, m), 1.75-1.9 (2H, m), 1.95-2.1 (2H, m), 2.2-2.38 (1H, m), 2.64-2.77 (1H, m), 7.52 (2H, d), 8.15 (2H, d); MS m/e (M−H)− 248.

Workup

  1. additionpoured onto ice
  2. extractionThe aqueous mixture was extracted with DCM
  3. concentrationthe organic layer was concentrated in vacuo
  4. customto leave a yellow oil, which
  5. customcrystallised to a white solid
  6. customThe solid was triturated with toluene
  7. filtrationfiltered

Sources & evidence

ORD record
ord-56ad983090704597890cb709d040ef6c
Source dataset
uspto-grants-2010_09
Patent number
US07795283B2

Reaction notes

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