1-Octanol → 1,3-Dioctyl glyceryl ether
Reaction equation
[CH2:1]([OH:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].CS(O)(=O)=O.[CH2:15]([O:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[CH:16]1[O:18][CH2:17]1>>[CH3:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH2:1][O:9][CH2:17][CH:16]([OH:18])[CH2:15][O:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]Participants
4
Conditions
- Temperature
- 95 °C
Procedure
Octyl alcohol (11.7 g; 0.09 mol) and methanesulfonic acid (0.50 g; 5.50 mmol) were placed in a 100-ml four-necked flask and heated up to 95° C. while stirring them under nitrogen. Octyl glycidyl ether (17.1 g; 0.09 mol) was then added dropwise over 10 minutes, and the resultant mixture was stirred for 8 hours as it was. After completion of the reaction, the reaction mixture was washed with a 4N aqueous solution (40 ml) of sodium hydroxide and additionally twice with water (40 ml) and then purified by column chromatography on silica gel (developing solvent: hexane) to obtain 2.0 g of 1,3-dioctyl glyceryl ether (9,13-dioxa-11-heneicosanol) as a colorless transparent oil (yield: 7%).
Workup
- customAfter completion of the reaction
- washthe reaction mixture was washed with a 4N aqueous solution (40 ml) of sodium hydroxide and additionally twice with water (40 ml)
- custompurified by column chromatography on silica gel (developing solvent: hexane)
Sources & evidence
- ORD record
- ord-c7d4f08806bb46589d017d955a7116db
- Source dataset
- uspto-grants-2001_03
- Patent number
- US06207845B1
Reaction notes
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