Nitrogen → 3,6,9,12-TETRAOXAHEPTADECAN-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][CH3:23]>>[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][CH3:23]Participants
5
Conditions
- Temperature
- 60 °C
Procedure
Tetraethyleneglycol (1087 g, 5.60 mol) was heated at 100° C. for 30 min with stirring and vigorous N2 bubbling, then cooled to 60° C. A 50% NaOH solution (61.6 g, 0.77 mol) was added and the resulting solution was heated at 100°-105° C. for 30 min with N2 bubbling. The solution was cooled to 60° C., bromopentane (106 g, 0.70 mol) was added, and the reaction was heated at 100°-110° C. for 24 hr. 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, and the solvent was removed in vacuo. The product (143 g, 78%) was a pale yellow oil.
Workup
- temperaturethe reaction was heated at 100°-110° C. for 24 hr
- temperatureThe reaction solution was cooled
- extractionextracted twice with methylene chloride
- washThe combined extracts were washed with 10% NaOH, water and brine
- customdried
- customthe solvent was removed in vacuo
Sources & evidence
- ORD record
- ord-fb3113534cfa4aa684f58489e4e11563
- Source dataset
- uspto-grants-1991_08
- Patent number
- US05041355
Reaction notes
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