a Farnesol → 3,7,11-Trimethyl-1-dodecanol
반응식
[OH:1][CH2:2][CH:3]=[C:4]([CH2:6][CH2:7][CH:8]=[C:9]([CH2:11][CH2:12][CH:13]=[C:14]([CH3:16])[CH3:15])[CH3:10])[CH3:5]>[Pd]>[CH3:5][CH:4]([CH2:6][CH2:7][CH2:8][CH:9]([CH3:10])[CH2:11][CH2:12][CH2:13][CH:14]([CH3:16])[CH3:15])[CH2:3][CH2:2][OH:1]참가 물질
3
시약·촉매·용매 1
반응 조건
- 온도
- 25 °C
실험 절차
Farnesol (572 g, 2.58 mole, 650 mL) was added to a 1000 mL Parr high pressure vessel containing 10% Pd/C (23 g, 4% by weight of farnesol). The reaction vessel was sealed and evacuated under house vacuum for 5 minutes after which time the reaction mixture was pressurized with H2 to 1000 psi. The reaction mixture was stirred at 25° C. and judged to be complete by thin layer chromatography (“TLC”, Rf=0.32, 90:10 hexane:ethyl acetate) after approximately 12 hours. The reaction vessel was depressurized under vacuum followed by venting to a N2 atmosphere. The reaction contents were vacuum filtered over a silica gel (60 Å from Aldrich) pad followed by washing of the silica gel with ethyl acetate (“EtOAc”, 3 L). The filtrate was concentrated on a rotary evaporator. The isolated product was further dried under high vacuum to remove any residual EtOAc to afford 3,7,11-trimethyldodecan-1-ol as a lightly tinted yellow viscous liquid. 1H-NMR (CDCl3, 500 MHz): δ 3.71 (m, 2H), 1.65-1.05 (m, 17H), 0.89-0.83 (overlapping t&d, 12H).