Water → HCID 16790146, compound

Reaction equation

O.[OH-].[Na+].Cl.[Cl:5][C:6]1[CH:7]=[C:8]([CH:10]=[CH:11][C:12]=1[O:13][CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[NH2:9]>C(O)C>[Cl:5][C:6]1[CH:7]=[C:8]([CH:10]=[CH:11][C:12]=1[O:13][CH2:14][CH2:15][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[NH2:9]

Participants

Procedure

To a mixture of water (50 ml), ethanol (50 ml) and 50% aqueous sodium hydroxide (25 ml) is added 3-chloro-4-(phenethyloxy)aniline hydrochloride (8.25 g; 0.0290 mol). When the solid is all dissolved, the solution is extracted with ether (3×100 ml). The ether solution is washed with brine, dried over potassium carbonate and concentrated under vacuum to yield 5.16 g (77%) of a tan oil. This oil is distilled at 140° C. under 0.005 mm vacuum to afford the product, a colorless liquid.