Ammonia → 2,3-Bis[(9Z)-9-octadecen-1-yloxy]-1-propanol
Reaction equation
N.C([C:20]([CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40]/[CH:41]=[CH:42]\[CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49]C)([OH:32])C(O)C(CC1C=CC=CC=1)O)CCCCCCC/C=C\CCCCCCCC.[CH3:51][CH2:52][OH:53].[CH2:54]1C[O:57][CH2:56][CH2:55]1>>[CH2:52]([O:53][CH2:54][CH:55]([CH2:56][OH:57])[O:32][CH2:20][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39]/[CH:40]=[CH:41]\[CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH3:49])[CH2:51][CH2:20][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37]/[CH:38]=[CH:39]\[CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH3:47]Participants
5
Conditions
- Temperature
- -65 °C
Procedure
A 250 ml flask equipped with a dry ice condenser and a dry ice-acetone bath was charged with anhydrous NH3 (140 ml). After cooling to -65° C. under N2 Li wire (1.35 g) was added in small pieces. Dioleylbenzylglycerol (10 g, 0.0146 mol) in THF (60 ml) and EtOH (12 g) was added over 30 minutes and then stirred at -65° C. for 15 minutes. The dry ice bath was removed and the reaction mass allowed to warm to room temperature, with evaporation of NH3. Water (100 ml) and heptane (150 ml) were added. The organic phase was washed with water, dried (MgSO4) and stripped of solvent yielding a light yellow oil (7.8 g, 90%).
Workup
- customA 250 ml flask equipped with a dry ice condenser and a dry ice-acetone bath
- additionwas added in small pieces
- customThe dry ice bath was removed
- temperatureto warm to room temperature, with evaporation of NH3
- additionWater (100 ml) and heptane (150 ml) were added
- washThe organic phase was washed with water
- dry with materialdried (MgSO4)
Sources & evidence
- ORD record
- ord-36cf45ebd60e4ffa9185e5d0c4878dfc
- Source dataset
- uspto-grants-1995_08
- Patent number
- US05439944
Reaction notes
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