[CH3:1][CH:2]1[CH2:7][CH2:6][C:5](=[O:8])[CH2:4][CH2:3]1.[NH2-].[Na+].Cl[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[O:18][CH3:19].N>O1CCCC1>[CH3:19][O:18][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[CH:4]1[CH2:3][CH:2]([CH3:1])[CH2:7][CH2:6][C:5]1=[O:8]4-Methylcyclohexanone (224 g, 2 moles) was added dropwise rapidly to a cooled, stirred suspension of 170 g (4 moles) of sodium amide in 2 l of tetrahydrofuran under nitrogen. After the addition was complete, the ice bath was removed and the mixture was heated at reflux until the evolution of ammonia ceased (~3 hours). While still at reflux, 142.5 g (1 mole) of o-chloroanisole was added rapidly dropwise and the mixture was heated for an additional hour, until evolution of ammonia ceased.
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