Ethylene Glycol → 2-(Pyridin-4-yloxy)ethanol
Reaction equation
[Na].Cl[C:3]1[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=1.C(=O)=O.[CH2:12]([OH:15])[CH2:13][OH:14]>>[OH:14][CH2:13][CH2:12][O:15][C:3]1[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=1Participants
5
Conditions
- Temperature
- -15 °C
Procedure
To a solution of sodium (9.2 g) in ethylene glycol (100 ml) was added portionwise 4-chloropyridine (39.6 g) under heating at 120° to 130° C. and stirring, which was continued for one hour at 130° C. after the addition. The mixture was cooled to -15° C. and dry ice (5.2 g) was added thereto. The mixture was warmed to 45° C. and allowed to stand at room temperature. The resulting precipitates were removed by filtration and washed with diisopropyl ether. The filtrate and washings were combined and evaporated. The residual oil was distilled to give 4-(2-hydroxyethoxy)pyridine (9 g), bp. 138° to 145° C. at 5 to 6 mmHg, which solidified and recrystallized from ethyl acetate. mp. 113° to 115° C. (dec.).
Workup
- temperatureunder heating at 120° to 130° C.
- additionafter the addition
- temperatureThe mixture was warmed to 45° C.
- customto stand at room temperature
- customThe resulting precipitates
- customwere removed by filtration
- washwashed with diisopropyl ether
- customevaporated
- distillationThe residual oil was distilled
Sources & evidence
- ORD record
- ord-320a36f774394774bc36da9db3e69a7f
- Source dataset
- uspto-grants-1985_06
- Patent number
- US04521413
Reaction notes
Loading…