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

HRID 1372914Notes

Reaction equation

HRID 1372914 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+]>CCCCCC.CCOC(C)=O.C1COCC1>[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) phenylmagnesium chloride (2 M in THF) are added dropwise at −50° C. to a solution of 20.0 g (80.32 mmol) 2-nitro-iodobenzene in abs. THF (150 mL) under a nitrogen atmosphere. After stirring for 15 min. 9.98 mL (96.30 mmol) cyclohexanone are added quickly. The mixture is heated to RT and stirred for a further 2 h. Sat. aqueous ammonium chloride solution is added and the aqueous phase is exhaustively extracted with EtOAc. The combined org. extracts are washed with sat. aqueous NaCl solution, dried with sodium sulphate 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 h
  2. extractionthe aqueous phase is exhaustively extracted with EtOAc
  3. washextracts are washed with sat. aqueous NaCl solution
  4. dry with materialdried with sodium sulphate
  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-43e58fe88ef34956b6bf6f7dd2fda5a6
Source dataset
uspto-grants-2007_01
Patent number
US07160882B2

Reaction notes

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