p-Toluenesulfonic acid → 4-(Hex-1-EN-1-YL)benzene-1,2-diol

Reaktionsgleichung

O1CCCCC1[O:7][C:8]1[CH:9]=[C:10]([CH:21]=[CH:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH:11]=[CH:12][C:13]=1[O:14]C1CCCCO1.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO.C(N(CC)CC)C>[OH:7][C:8]1[CH:9]=[C:10]([CH:21]=[CH:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH:11]=[CH:12][C:13]=1[OH:14]

Komponenten

Versuchsvorschrift

In 10 ml of absolute methanol was dissolved 198 mg of 1-(3',4'-bistetrahydropyranyloxy-phenyl)-1-hexene obtained in Example 17-(1), and a catalytic amount of p-toluenesulfonic acid was added to the solution at 0° C. The mixture was stirred for 2 hours at the same temperature. After reaction, one drop of triethylamine was added to the reaction mixture and the mixture was concentrated to give crude product. By purification of the crude product by means of column chromatography [silica gel/ether:hexane (1:2)], 61 mg of pure product was obtained.