Reaction equation
C([O:3][C:4](=[O:26])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH:24]=[CH2:25])C.[OH-:27].[Na+].OO.Cl>O.C1COCC1>[OH:27][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][C:4]([OH:3])=[O:26]Participants
Conditions
- Temperature
- 0 °C
Procedure
22-Hydroxy-docosanoic acid was synthesized according to Mori et al., Liebigs Ann. Chem., (1991), 253-257. Briefly, under N2 atmosphere 6.6 g Docos-21-enoic acid ethyl ester and 30 ml THF were combined and cooled down to 0° C. Then 0.5 eq. (9 ml) borane/THF complex was added dropwise and the mixture was allowed to stir for 2 hours at room temperature. After the addition of 1.2 ml H2O the suspension was again cooled down to 0° C. and 15 ml 3M NaOH and 2 ml 35% H2O2 were added. The mixture was stirred for one hour at 50° C. Then the temperature was brought to room temperature and the pH was adjusted to pH 2-3 with 2N HCl. The solid was fritted, washed with H2O, codistilled three times with CHCl3 and recrystallized from CHCl3. After a further treatment with NaOH (3M in H2O) in THF at 50° C. over 1.5 days the pH was again adjusted to pH 2-3 and the crude product was fritted, washed with H2O and codistilled two times with CHCl3. The product was characterized by thin layer chromatography and 1H-NMR.
Workup
- additionThen 0.5 eq. (9 ml) borane/THF complex was added dropwise
- additionwere added
- stirringThe mixture was stirred for one hour at 50° C
- customwas brought to room temperature
- washwashed with H2O
- customrecrystallized from CHCl3
- waitAfter a further treatment with NaOH (3M in H2O) in THF at 50° C. over 1.5 days the pH was again adjusted to pH 2-3
- washwashed with H2O
Sources & evidence
- ORD record
- ord-04862cbc8f40475e9a9b4c04188ddee9
- Source dataset
- uspto-grants-2012_06
- Patent number
- US08193246B2
Linked notes
Loading…