O1CCCCC1[O:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]Br.O1CCCCC1[O:26][C:27]1[CH:32]=[CH:31][C:30]([Mg]Br)=[CH:29][CH:28]=1.O1CCCCC1OC1C=CC(Br)=CC=1.[Mg]>O1CCCC1.Cl[Cu].C(OCC)C>[OH:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:30]1[CH:29]=[CH:28][C:27]([OH:26])=[CH:32][CH:31]=1
0.4 g of CuCl and 29 g of 11-(tetrahydropyran-2-yloxy)-1-bromoundecane (B) were added to a filtered solution of 4-(tetrahydropyran-2-yloxy)phenyl magnesium bromide (A), prepared from 20.0 g of 4-(tetrahydropyran-2-yloxy)-1-bromobenzene and 3.16 g of magnesium, in 100 ml of tetrahydrofuran. After refluxing for 2 days, the reaction mixture was mixed with 100 ml of diethyl ether, followed by extraction with 100 ml of a saturated NH4Cl solution. After evaporation, the intermediate product C was refluxed for one hour with 40 ml of methanol and 1 ml of saturated hydrochloric acid. 15 ml of a saturated solution of NaHCO3 was added and the methanol was evaporated. 100 ml of diethyl ether was added. 7.4 g of 4-(11-hydroxyundecyl) phenol (D, 36%) was obtained after extraction with 50 ml of saturated sodium chloride, drying over magnesium sulphate, evaporation and recrystallisation from toluene.
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