Water → 4-[3-(Octadecyloxy)propoxy]butanol
Reaction equation
[H-].[Na+].[CH2:3]([OH:8])[CH2:4][CH2:5][CH2:6][OH:7].CS(O[CH2:14][CH2:15][CH2:16][O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])(=O)=O.O>CS(C)=O>[CH2:18]([O:17][CH2:16][CH2:15][CH2:14][O:7][CH2:6][CH2:5][CH2:4][CH2:3][OH:8])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
Sodium hydride (1.2 g) is heated at 70° C. for 10 minutes in dimethyl sulfoxide (50 ml), to which is added 1,4-butanediol (4.5 g). The mixture is heated for one further hour. To this reaction mixture is added dropwise a solution of 3-(octadecyloxy)propyl methanesulfonate obtained in Reference Example 1 (4.06 g) in dimethyl sulfoxide (15 ml), and the mixture is stirred at 70° C. for one hour. The reaction mixture is poured into cold water, and the mixture is subjected to extraction with a mixture of hexane and ethyl acetate. The extract is washed with water and then dried, and the solvents are then distilled off under reduced pressure. The residue is subjected to purification by means of silica gel column chromatography to obtain the above-titled compound (2.2 g).
Workup
- temperatureThe mixture is heated for one further hour
- extractionthe mixture is subjected to extraction with a mixture of hexane and ethyl acetate
- washThe extract is washed with water
- customdried
- distillationthe solvents are then distilled off under reduced pressure
- customThe residue is subjected to purification by means of silica gel column chromatography
Sources & evidence
- ORD record
- ord-220cf47fe04b4b33a4de16b39a8fce54
- Source dataset
- uspto-grants-1991_04
- Patent number
- US05008454
Reaction notes
Loading…