Water → HCID 178444450, Verbindung

Reaktionsgleichung

C([O:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13][CH2:14][CH2:15][C@H:16]2[CH2:21][CH2:20][C@H:19]([CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH2:18][CH2:17]2)=[CH:8][CH:7]=1)CCC.B(Br)(Br)Br.O>ClCCl>[CH2:22]([C@H:19]1[CH2:18][CH2:17][C@H:16]([CH2:15][CH2:14][CH2:13][CH2:12][C:9]2[CH:8]=[CH:7][C:6]([OH:5])=[CH:11][CH:10]=2)[CH2:21][CH2:20]1)[CH2:23][CH2:24][CH2:25][CH3:26]

Komponenten

Versuchsvorschrift

A mixture of 16 g of 1-butyloxy-4-[4-(trans-4-pentylcyclohexyl)-1-butyl]benzene and 100 ml of absolute dichloromethane was treated at 0° C. and while gassing with nitrogen with 50 ml of a 1M solution of boron tribromide in dichloromethane. After completion of the addition the reaction mixture was stirred at room temperature for a further 2 hours and then treated cautiously with 200 ml of water. The organic phase was separated and the aqueous phase was back-extracted three times with 100 ml of dichloromethane each time. The combined organic phases were washed in succession with 1000 ml of water, 500 ml of dilute potassium carbonate solution and again with 1000 ml of water, dried over magnesium sulfate, filtered and subsequently concentrated. Recrystallization of the residue from hexane gave 11 g of pure 4-[4-(trans-4-pentylcyclohexyl)-1-butyl]phenol with m.p. 86° C.