3,7,11,15-tetramethylhexadecan-1-ol

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Hydrogenation of phytol can also be accomplished using Raney nickel and hydrogen to yield phytanol as referenced in Bendavid, A., Burns, C. J., Leslie, D. F., Hashimoto, K., Ridley, D. D., Sandanayake, S., and Wieczorek L., J. Org. Chem. (2001), 66, 3709-3716; Kim, T., Chan, K. C, and Crooks, R. M., J. Am. Chem. Soc. (1997) 119, 189; and Jellum, E., Eldjarn, L., and Try, K., Acta Chem. Scand. (1966), 20, 2335.

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Phytol (30.0 g, 0.101 mol) was dissolved in 200 ml of ethanol. A suspension of 1.8 g of Raney-Ni (W-1) in 5 ml of ethanol was added thereto, and hydrogenation was carried out under hydrogen for about 5 hours so that 2405 ml of hydrogen (theoretical volume at 24° C.; 2465 ml) was absorbed. After filtering off the catalyst through a filter paper, the ethanol was evaporated. Yield 29.9 g. Silica gel column chromatography with benzene-hexane (1:1) gave 24.7 g of the title compound (yield 82.3%). was added was absorbed After filtering off the catalyst through a filter paper the ethanol was evaporated

Conditions: temp:-15.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Phytanol (22) (20.0 g, 66.7 mmol), triethylamine (18.6 mL, 133 mmol) and a stir bar were added to a 1000 mL round bottom flask. The flask was sealed and flushed with nitrogen. Anhydrous DCM (250 mL) was added, and the mixture cooled to −15° C. (Ice and NaCl). Mesyl Chloride (10.4 mL, 133 mmol) was added slowly via syringe over a 30 minute period, and the reaction stirred at −15° C. for a further 1.5 hours. At this point TLC showed that the starting material had been used up. The solution was diluted with DCM (250 mL) and washed with saturated NaHCO3 (2×200 mL) The organic phase was then dried (MgSO4), filtered and concentrated (rotovap). The crude product was purified by column chromatography. Yield 21.5 g, 85.7%. The flask was sealed flushed with nitrogen Anhydrous DCM (250 mL) was added washed with saturated NaHCO3 (2×200 mL) The organic phase was then dried (MgSO4) filtered concentrated (rotovap) The crude product was purified by column chromatography

Conditions: temp:-15.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Phytanol (22) (20.0 g, 66.7 mmol), triethylamine (18.6 mL, 133 mmol) and a stir bar were added to a 1000 mL round bottom flask. The flask was sealed and flushed with nitrogen. Anhydrous DCM (250 mL) was added, and the mixture cooled to −15° C. (Ice and NaCl). Mesyl Chloride (10.4 mL, 133 mmol) was added slowly via syringe over a 30 minute period, and the reaction stirred at −15° C. for a further 1.5 hours. At this point TLC showed that the starting material had been used up. The solution was diluted with DCM (250 mL) and washed with saturated NaHCO3 (2×200 mL) The organic phase was then dried (MgSO4), filtered and concentrated (rotovap). The crude product was purified by column chromatography. Yield 21.5 g, 85.7%. The flask was sealed flushed with nitrogen Anhydrous DCM (250 mL) was added washed with saturated NaHCO3 (2×200 mL) The organic phase was then dried (MgSO4) filtered concentrated (rotovap) The crude product was purified by column chromatography

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 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. the flask sealed flushed with hydrogen to bubble hydrogen through the solution for 10 minutes 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 200 mL of DCM added to the resulting oil The solution was washed with water (2×100 mL) dried over MgSO4 concentrated

Conditions: temp:-15.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Phytanol (22) (20.0 g, 66.7 mmol), triethylamine (18.6 mL, 133 mmol), and a stir bar were added to a 1000 mL round bottom flask. The flask was sealed and flushed with nitrogen. Anhydrous DCM (250 mL) was added, and the mixture cooled to −15° C. (ice and NaCl). Mesyl Chloride (10.4 mL, 133 mmol) was added slowly via syringe over a 30 minute period, and the reaction stirred at −15° C. for a further 1.5 hours. At this point TLC showed that the starting material had been used up. The solution was diluted with DCM (250 mL) and washed with saturated NaHCO3 (2×200 mL). The organic phase was then dried (MgSO4), filtered, and concentrated (rotovap). The crude product was purified by column chromatography. Yield: 21.5 g, 85.7%. The flask was sealed flushed with nitrogen Anhydrous DCM (250 mL) was added washed with saturated NaHCO3 (2×200 mL) The organic phase was then dried (MgSO4) filtered concentrated (rotovap) The crude product was purified by column chromatography