Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH:8]=[CH2:9].[OH:10][C:11]1[CH:21]=[CH:20][C:14]([C:15]([O:17]CC)=[O:16])=[CH:13][CH:12]=1.C(=O)([O-])[O-].[K+].[K+].[OH-].[Na+].Cl>C(O)C.O>[CH2:2]([O:10][C:11]1[CH:21]=[CH:20][C:14]([C:15]([OH:17])=[O:16])=[CH:13][CH:12]=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH:8]=[CH2:9]
9.4 g of 8-bromo-1-octene, 9.0 g of ethyl p-hydroxybenzoate, and 7.6 g of potassium carbonate were refluxed in ethanol for 10 hours. Added thereto was an aqueous solution containing 2.4 g of sodium hydroxide, and reflux was further continued for 10 hours. After conclusion of the reaction, the reaction solution was diluted with water, and the pH of the diluted solution was lowered to 2 by dropping hydrochloric acid thereto. The generated precipitate was collected, and was then washed with water sufficiently and dried, to obtain 10.8 g of the objective ether compound. (Yield: 89%)
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