Reaction equation
[Cl:1][CH:2]([CH2:6][OH:7])[C:3]([OH:5])=[O:4].[F:8][C:9]([F:35])([C:13]([F:34])([F:33])[C:14]([F:32])([F:31])[C:15]([F:30])([F:29])[C:16]([F:28])([F:27])[C:17]([F:26])([F:25])[C:18]([F:24])([F:23])[C:19]([F:22])([F:21])[F:20])[CH2:10][CH2:11]O.Cl>C(OCC)C>[F:8][C:9]([F:35])([C:13]([F:33])([F:34])[C:14]([F:31])([F:32])[C:15]([F:29])([F:30])[C:16]([F:27])([F:28])[C:17]([F:25])([F:26])[C:18]([F:24])([F:23])[C:19]([F:22])([F:21])[F:20])[CH2:10][CH2:11][O:4][C:3](=[O:5])[CH:2]([Cl:1])[CH2:6][OH:7]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 65 °C
Procedure
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).
Workup
- washwashed twice with 100 mL of dil. NaHCO3 aq. sol. and once with 100 mL of sat. aq. NaCl sol.
- customdried over anhy
- filtrationSolution was filtered
- customsolvent was removed by rotary evaporation and unreacted alcohol
- customwas sublimed off at 70° C. under vacuum
Sources & evidence
- ORD record
- ord-677c3e9dab1e457ca7d7d2c5e85e43ce
- Source dataset
- uspto-grants-2013_09
- Patent number
- US08524942B2
Linked notes
Loading…