Cyclohexanone → 1-(2-Nitrophenyl)cyclohexan-1-ol

HRID 1867333Notes

Reaction equation

HRID 1867333 reaction equation
C1([Mg]Cl)C=CC=CC=1.[N+:9]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1I)([O-:11])=[O:10].[C:19]1(=[O:25])[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1.[Cl-].[NH4+]>C1COCC1.CCCCCC.CCOC(C)=O>[N+:9]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:19]1([OH:25])[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1)([O-:11])=[O:10]

Participants

7

Reactant 4

HCID 7967CyclohexanoneHCID 25517Ammonium ChlorideHCID 69115o-IodonitrobenzeneHCID 178478979HCID 178478979, compound

Product 1

HCID 210728061-(2-Nitrophenyl)cyclohexan-1-ol

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

40.16 mL (80.32 mmol) of phenylmagnesium chloride (2 M in THF) is added dropwise at −50° C. to a solution of 20.0 g (80.32 mmol) of 2-nitroiodobenzene in absolute THF (150 mL) under a nitrogen atmosphere. After stirring for 15 minutes, 9.98 mL (96.30 mmol) of cyclohexanone is added quickly. The mixture is heated to RT and stirred for a further 2 hours. Saturated aqueous ammonium chloride solution is added and the aqueous phase is exhaustively extracted with EtOAc. The combined organic extracts are washed with saturated aqueous NaCl solution, dried with sodium sulfate, and evaporated down in vacuo. After column chromatography (silica gel, hexane/EtOAc 20:1), the product is obtained as a brownish oil. Yield: 5.20 g (29%); Rf=0.26 (silica gel, hexane/EtOAc 10:1); ESI-MS: [M+H—H2O]+=204.

Workup

  1. stirringstirred for a further 2 hours
  2. extractionthe aqueous phase is exhaustively extracted with EtOAc
  3. washThe combined organic extracts are washed with saturated aqueous NaCl solution
  4. dry with materialdried with sodium sulfate
  5. customevaporated down in vacuo
  6. customAfter column chromatography (silica gel, hexane/EtOAc 20:1), the product is obtained as a brownish oil

Sources & evidence

ORD record
ord-cb5d82a5ce924336ab9932c242ff52c4
Source dataset
uspto-grants-2009_12
Patent number
US07632834B2

Reaction notes

Loading…