Sulfuric Acid → 1,1'-Oxydi(butan-2-ol)
Reaction equation
[CH2:1]([OH:6])[CH:2]([OH:5])[CH2:3][CH3:4].[Na].[O:8]1[CH:10]([CH2:11][CH3:12])[CH2:9]1.S(=O)(=O)(O)O>>[OH:5][CH:2]([CH2:3][CH3:4])[CH2:1][O:6][CH2:9][CH:10]([OH:8])[CH2:11][CH3:12]Participants
Conditions
- Temperature
- 100 °C
Procedure
A 500 ml, three neck, round bottom flask equipped with magnetic stirrer, internal thermometer, addition funnel, condenser, argon supply, and heating mantle, is flushed with argon. Then 1,2-butanediol (about 270 g, about 3 moles, Aldrich) is added and sodium metal (about 1.2 g, about 0.05 moles, Aldrich) is added and the sodium is allowed to dissolve. Then the reaction mixture is heated to about 100° C. and epoxybutane (about 71 g. about 1 mole, Aldrich) is added dropwise with stirring. Heating is continued until the reflux of epoxybutane has ceased and heating is continued for an additional hour to drive the conversion to completion. The reaction mixture is neutralized with sulfuric acid, the salts are removed by filtration, and the liquid is fractionally distilled under vacuum to recover the excess butanediol. The desired ether is obtained as a residue. Optionally, it is purified by further vacuum distillation.
Workup
- customA 500 ml, three neck, round bottom flask equipped with magnetic stirrer
- additioninternal thermometer, addition funnel, condenser, argon supply
- temperatureheating mantle
- customis flushed with argon
- dissolutionto dissolve
- temperatureHeating
- temperatureheating
- waitis continued for an additional hour
- customthe salts are removed by filtration
- distillationthe liquid is fractionally distilled under vacuum
- customto recover the excess butanediol
- customThe desired ether is obtained as a residue
- distillationOptionally, it is purified by further vacuum distillation
Sources & evidence
- ORD record
- ord-578e3d4f72d342daa0d34c6b1a83e9f9
- Source dataset
- uspto-grants-2001_11
- Patent number
- US06323172B1
Reaction notes
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