4-Methylcyclohexanone → 2-(3-Methoxyphenyl)-4-methylcyclohexan-1-one

HRID 904762Notes

Reaction equation

HRID 904762 reaction equation
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][CH3:9].[NH2-].[Na+].[CH3:12][CH:13]1[CH2:18][CH2:17][C:16](=[O:19])[CH2:15][CH2:14]1>O1CCCC1>[CH3:9][O:8][C:3]1[CH:4]=[C:5]([CH:15]2[CH2:14][CH:13]([CH3:12])[CH2:18][CH2:17][C:16]2=[O:19])[CH:6]=[CH:7][CH:2]=1

Participants

5

Reactant 3

HCID 115254-MethylcyclohexanoneHCID 130112-ChloroanisoleHCID 24533Sodium amide

Product 1

HCID 132820202-(3-Methoxyphenyl)-4-methylcyclohexan-1-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Employing the general procedure of T. Kametani, et al., J. Chem. Soc. (C), 1971, 1047, 187 g o-chloroanisole was added to a mixture of 215 g of sodium amide, 3 liters of anhydrous tetrahydrofuran and 400 g of 4-methylcyclohexanone. The reaction was refluxed for 18 hours then quenched with saturated ammonium chloride. Concentration of the organic phase, dilution with water, extraction with ether and distillation of the residue from concentrating the ether extracts gave 90 g, b.p. 135° (0.07 mm), of product.

Workup

  1. temperatureThe reaction was refluxed for 18 hours
  2. customthen quenched with saturated ammonium chloride
  3. extractionConcentration of the organic phase, dilution with water, extraction
  4. distillationwith ether and distillation of the residue
  5. concentrationfrom concentrating the ether
  6. customextracts gave 90 g, b.p. 135° (0.07 mm)

Sources & evidence

ORD record
ord-3e95050b67514cf38f613d7231b35926
Source dataset
uspto-grants-1983_12
Patent number
US04419517

Reaction notes

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