Cyclohexanone → 2-(3-Methoxyphenyl)cyclohexanone

HRID 1594918Notes

Reaction equation

HRID 1594918 reaction equation
[Li]CCCC.CCCCCC.CC1(C)CCCC(C)(C)N1.[C:22]1(=[O:28])[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1.Cl[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[O:36][CH3:37]>C1COCC1>[CH3:37][O:36][C:31]1[CH:32]=[C:33]([CH:23]2[CH2:24][CH2:25][CH2:26][CH2:27][C:22]2=[O:28])[CH:34]=[CH:35][CH:30]=1

Participants

7

Reactant 5

HCID 7967CyclohexanoneHCID 8058Hexane2×HCID 130112-ChloroanisoleHCID 130352,2,6,6-TetramethylpiperidineHCID 178418339Butyllithium2×

Product 1

HCID 858682-(3-Methoxyphenyl)cyclohexanone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 1.6 M n-BuLi in hexane (12.5 mL, 20 mmol) at 0° C. was added a solution of 2,2,6,6-tetramethyl piperidine (3.4 mL, 20 mmol) in anhydrous THF (40 mL) over 5 min. Cyclohexanone (2.1 mL, 20 mmol) was added dropwise. After stirring the reaction mixture for 10 min, a further portion of 1.6M n-BuLi in hexane (12.5 mL, 20 mmol) was added, the mixture stirred for 10 min, and 2-chloroanisole (2.5 mL, 20 mmol) was added. After stirring for 30 min under Ar, the reaction mixture was quenched with H2O (300 mL) and extracted with EtOAc (150 mL). The organic layer was separated, washed with 2N HCl (100 mL), H2O (200 mL) and brine, then dried (MgSO4). Filtration and concentration gave the title compound after SiO2 chromatography (CHCl3:MeOH, 200:1).

Workup

  1. stirringthe mixture stirred for 10 min
  2. stirringAfter stirring for 30 min under Ar
  3. customthe reaction mixture was quenched with H2O (300 mL)
  4. extractionextracted with EtOAc (150 mL)
  5. customThe organic layer was separated
  6. washwashed with 2N HCl (100 mL), H2O (200 mL) and brine
  7. dry with materialdried (MgSO4)
  8. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-6017d39c97474be28d07049406d238ed
Source dataset
uspto-grants-2001_09
Patent number
US06284755B1

Reaction notes

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