[CH2:1]([C:4]1[C:10]([OH:11])=[CH:9][CH:8]=[C:7]([CH2:12][CH:13]=[CH2:14])[C:5]=1[OH:6])[CH:2]=[CH2:3]>CO.[Pd]>[CH2:1]([C:4]1[C:5]([OH:6])=[C:7]([CH2:12][CH2:13][CH3:14])[CH:8]=[CH:9][C:10]=1[OH:11])[CH2:2][CH3:3]The product 2,6-bis-allylresorcinol (33.5 gm) was dissolved in methanol and hydrogenated under H2 Pressure (initial pressure 45 psig) over 10% Pd on carbon (300 mg). The reaction mixture was filtered through celite and reduced i. vac. The crude oil was flushed through a short SiO2 gel column eluting with ethyl ether. The resulting oil was purified by crystallization from hexanes:ether.
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