[CH3:1][C:2]1[CH:8]=[C:7]([C:9]([CH2:12][C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:11])[CH3:10])[CH:6]=[C:4]([OH:5])[C:3]=1[OH:17].[O:18]1[C:20]([CH3:25])([CH2:21][CH2:22][CH:23]=[CH2:24])[CH2:19]1.N1CCCCC1>CCOCC>[OH:18][C:20]([CH3:25])([CH2:21][CH2:22][CH:23]=[CH2:24])[CH2:19][O:5][C:4]1[CH:6]=[C:7]([C:9]([CH2:12][C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:11])[CH3:10])[CH:8]=[C:2]([CH3:1])[C:3]=1[OH:17]A mixture of 10.5 g (44 mmole) of 3-methyl-5-t-octylcatechol, 11 g (90 mmole) of 1,2-epoxy-2-methyl-5-hexene and 0.75 ml of piperidine was heated at 120° C., with stirring, under nitrogen, for 7 days. The reaction mixture was cooled and dissolved in ether (300 ml), and the resulting solution was washed with water, followed by 1N hydrochloric acid, followed by saturated sodium chloride solution. The washed ethereal solution was dried (MgSO4) and evaporated in vacuo, and the residue was purified by column chromatography on silica gel, eluting with chloroform. This afforded a 25% yield of the title compound as an oil.
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