Nitrogen → 3,6,9,12-Tetraoxaeicosan-1-ol
Reaction equation
[CH2:1]([OH:13])[CH2:2][O:3][CH2:4][CH2:5][O:6][CH2:7][CH2:8][O:9][CH2:10][CH2:11][OH:12].N#N.[OH-].[Na+].Br[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]>>[CH2:19]([O:12][CH2:11][CH2:10][O:9][CH2:8][CH2:7][O:6][CH2:5][CH2:4][O:3][CH2:2][CH2:1][OH:13])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]Participants
5
Conditions
- Temperature
- 60 °C
Procedure
Tetraethyleneglycol (1243 g, 6.40 mol) was heated at 100° C. for 30 minutes with stirring and vigorous N2 bubbling, then cooled to 60° C. A 50% NaOH solution (70.4 g, 0.88 mol) was added and the resulting solution was heated at 100°-105° C. for 30 minutes with N2 bubbling. The solution was cooled to 60° C., bromooctane (154 g, 0.80 mol) was added, and the reaction was heated at 100°-110° C. for 24 hours. The reaction solution was cooled, added to ice water and extracted twice with methylene chloride. The combined extracts were washed with 10% NaOH, water and brine; dried, treated with charcoal, and filtered through a thin silica gel pad. The solvent was removed in vacuo; the residual product (155 g, 63%) was a pale yellow oil.
Workup
- temperaturethe reaction was heated at 100°-110° C. for 24 hours
- temperatureThe reaction solution was cooled
- extractionextracted twice with methylene chloride
- washThe combined extracts were washed with 10% NaOH, water and brine
- customdried
- additiontreated with charcoal
- filtrationfiltered through a thin silica gel pad
- customThe solvent was removed in vacuo
Sources & evidence
- ORD record
- ord-ac3b16678f6c49a0b2eeeca8d862309d
- Source dataset
- uspto-grants-1991_01
- Patent number
- US04988604
Reaction notes
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