[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([OH:11])=O.Cl.[NH2:13][OH:14].C[O-].[Na+].C(=O)([O-])[O-].[K+].[K+].Br[CH2:25][CH2:26]Br>CO.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(OCC)(=O)C.C1(C)C=CC=CC=1.O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]1[O:11][CH2:26][CH2:25][O:14][N:13]=1A solution of 5.0 g (29.3 mmole) of o-chlorophenylacetic acid and 0.3 g of p-toluenesulfonic acid monohydrate in 50 ml of methanol was heated under reflux for 6 hours. At the end of this time, 3.1 g (44 mmole) of hydroxylamine hydrochloride were added to the reaction mixture, followed by 2.1 g of sodium methoxide. The resulting reaction mixture was then heated under reflux for 10 hours. 14.2 g (103 mmole) of potassium carbonate and 5.1 ml of 1,2-dibromoethane were then added to the resulting reaction mixture, followed by 15 ml of water. The reaction mixture was then heated under reflux for a further 10 hours. At the end of this time, 200 ml of ethyl acetate were added to the reaction mixture, and the organic layer was separated, washed with a saturated aqueous solution of sodium hydrogencarbonate and dried over anhydrous sodium sulfate; the solvent was then removed by distillation under reduced pressure. The residue thus obtained was subjected to silica gel column chromatography, using a 9:1 by volume mixture of toluene and ethyl acetate as the eluent, to give 4.9 g of the title compound as an oil.
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