Реакция #2348079

Уравнение реакции

Farnesol

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3,7,11-trimethyldodecan-1-ol

Условия реакции

Обработка

1. 1
   ДругоеThe reaction vessel was sealed
2. 2
   Другоеevacuated under house vacuum for 5 minutes after which time the reaction mixture
3. 3
   ДругоеThe reaction contents
4. 4
   Фильтрацияfiltered over a silica gel (60 {acute over (Å)} from Aldrich) pad
5. 5
   Промывкаby washing of the silica gel with ethyl acetate (“EtOAc”, 3 L)
6. 6
   КонцентрированиеThe filtrate was concentrated on a rotary evaporator
7. 7
   ДругоеThe isolated product was further dried under high vacuum
8. 8
   Другоеto remove any residual EtOAc

Методика

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 {acute over (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).

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