N([O-])=O.[Na+].N[CH:6]1[CH:12]([CH2:13][C:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:15])[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1.[ClH:22]>O.[Cu]Cl>[Cl:22][CH:6]1[CH:12]([CH2:13][C:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:15])[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1A solution of 5 g of sodium nitrite in 20 ml of water is slowly added dropwise at 0°C, whilst stirring, to a solution of 11 g of crude 3-amino-4-cycloheptyl-acetophenone in 70ml of concentrated hydrochloric acid. After completion of the addition the mixture is stirred for a further 30 minutes at 0°C. The reaction solution is then added dropwise at 0 to 5°C, whilst stirring, to a solution of 7 g of freshly prepared copper-(I) chloride in 30 ml of concentrated hydrochloric acid. After completion of the addition, the mixture is stirred for a further hour at room temperature and a further hour at 40 to 50°C. The reaction mixture is now extracted three times with 200 ml of ether at a time. The organic phases are successively washed with water, 2 N sodium hydroxide solution and again with water, dried over sodium sulphate and evaporated in vacuo. Distillation of the evaporation residue in a high vacuum yields crude 3-chloro-4-cycloheptyl-acetophenone in the fraction boiling at about 130°C/0.05 mm Hg.
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