Ethanol → Dihydrophytol

Phytol (21.0 g, 70.8 mmol), ethanol (180 mL) and a stir bar were added to a 500 mL round bottom flask. Raney Nickel 2800 (as purchased, a 50% by weight solution in water if used as purchased, Nickel>89% metal present) (6.8 g, 51.5 mmol) was added, and the flask sealed and flushed with hydrogen. A 12″ needle was used to bubble hydrogen through the solution for 10 minutes. The reaction was stirred for 5 days, using a balloon as a hydrogen reservoir. Hydrogen was also bubbled through the reaction mixture at 24 h and 48 h, 5 minutes each time. The metal catalyst was then removed by filtering through Celite. The ethanolic solution was concentrated, and 200 mL of DCM added to the resulting oil. The solution was washed with water (2×100 mL), dried over MgSO4, and concentrated. TLC indicated formation of the phytanol product, yield 20.0 g.

1. customthe flask sealed
2. customflushed with hydrogen
3. customto bubble hydrogen through the solution for 10 minutes
4. customHydrogen was also bubbled through the reaction mixture at 24 h and 48 h, 5 minutes each time
5. customThe metal catalyst was then removed
6. filtrationby filtering through Celite
7. concentrationThe ethanolic solution was concentrated
8. addition200 mL of DCM added to the resulting oil
9. washThe solution was washed with water (2×100 mL)
10. dry with materialdried over MgSO4
11. concentrationconcentrated

ORD record

ord-0031575d01954ee08a3641104204c04a

Source dataset

uspto-grants-2014_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08716464B2