Réaction #67774

Équation de réaction

2-chloro-3-hydroxypropionic acid

3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluoro-1-decanol

hydrochloric acid

→

(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluoro-1-decyl)-2-chloro-3-hydroxypropionate

Solvants

ethyl ether

Conditions de réaction

Traitement

1. 1
   Lavagewashed twice with 100 mL of dil. NaHCO3 aq. sol. and once with 100 mL of sat. aq. NaCl sol.
2. 2
   Autredried over anhy
3. 3
   FiltrationSolution was filtered
4. 4
   Autresolvent was removed by rotary evaporation and unreacted alcohol
5. 5
   Autrewas sublimed off at 70° C. under vacuum

Mode opératoire

In a 50 mL RB with a condenser, 2-chloro-3-hydroxypropionic acid (6.0 g, 0.05 mol) and 3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluoro-1-decanol (18.0 g, 0.04 mol) and a catalytic amount of hydrochloric acid were taken together and heated up to 65° C. for 36 h. Product was dissolved in 300 mL of ethyl ether and washed twice with 100 mL of dil. NaHCO3 aq. sol. and once with 100 mL of sat. aq. NaCl sol. and then dried over anhy. Na2SO4. Solution was filtered, solvent was removed by rotary evaporation and unreacted alcohol was sublimed off at 70° C. under vacuum. Yield=15.0 g (67%). 1H-NMR (CDCl3, 7.27 ppm): 2.54 (m, —CH2CF2). 3.05-3.35 (broad, —OH), 4.01 (m, —CH2OH), 4.42 (m, —CHCl), 4.52 (m, —CO2CH2CH2).

Source