1-Octanol → 1,3-Dioctyl glyceryl ether

HRID 1533484Notes

Reaction equation

[CH2:1]([OH:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[Al].[CH2:11]([O:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[CH:12]1[O:14][CH2:13]1>C1C(O)=CC=C(S(O)(=O)=O)C=1>[CH3:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH2:1][O:9][CH2:13][CH:12]([OH:14])[CH2:11][O:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]

Participants

Conditions

Temperature: 95 °C

Procedure

Octyl alcohol (11.7 g; 0.09 mol), aluminum triisopropxide (0.36 g; 1.77 mmol) and p-phenolsulfonic acid (0.94 g; 5.40 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 3 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 vacuum distillation to obtain 23.0 g of 1,3-dioctyl glyceryl ether (9,13-dioxa-11-heneicosanol) as a colorless transparent oil (yield: 81%).

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)
distillationpurified by vacuum distillation

Sources & evidence

ORD record: ord-d780ee2061534b849bc223865bdf9729
Source dataset: uspto-grants-2001_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06207845B1

Reaction notes

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