Reaction #2348136

Reaction equation

phytanol

phytanol

pyridine

p-toluenesulfonyl chloride

→

phytanyl tosylate

Yield 138.7%

Solvents

methylene chloride

Conditions

Workup

1. 1
   Otherfrom exceeding 10° C
2. 2
   workup.ADDITIONAfter the completion of addition, agitation
3. 3
   Otherthe resulting reaction solution
4. 4
   Washwas successively washed with 200 ml of water, 200 ml of 2N hydrochloric acid, and 200 ml of a saturated sodium bicarbonate water
5. 5
   Dryingdried over anhydrous magnesium sulfate
6. 6
   FiltrationAfter the filtration
7. 7
   Concentrationthe resultant was concentrated under reduced pressure

Procedure

Under a nitrogen atmosphere, 29.16 g (97.67 mmol) of phytanol and 9.27 g (117.2 mmol) of pyridine were dissolved in 220 ml of dry methylene chloride, and 20.48 g (107.4 mmol) of p-toluenesulfonyl chloride was added little by little under ice cooling, in order to prevent the liquid temperature from exceeding 10° C. After the completion of addition, agitation was continued for 12 hours until phytanol disappeared, the resulting reaction solution was successively washed with 200 ml of water, 200 ml of 2N hydrochloric acid, and 200 ml of a saturated sodium bicarbonate water, and dried over anhydrous magnesium sulfate. After the filtration, the resultant was concentrated under reduced pressure to obtain 61.31 g of phytanyl tosylate.

Source