[OH:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[Cl:9].[OH-].[Na+].[CH2:12](Br)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23].Cl>C(O)C>[CH2:23]([O:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[Cl:9])[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH3:12]In ethanol was dissolved 5.0 g of 4-hydroxy-3-chlorophenol, and an aqueous solution of 1.38 g of sodium hydroxide and 8.6 g of n-dodecyl bromide were added to the solution under reflux in a nitrogen atmosphere. The mixture was refluxed for 6 hours and cooled, and the thus-obtained solution was put into a 1N aqueous solution of hydrochloric acid and extracted with chloroform. The extract was washed with a saturated aqueous solution of sodium chloride, dehydrated on anhydrous magnesium sulfate and concentrated. The concentrate was purified by using a silica gel column to obtain 1.73 g of 4-dodecyloxy-3-chlorophenol.
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