Pyridine → 9-Octadecene, 1-chloro-
Reaction equation
[CH2:1](O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].N1C=CC=CC=1.S(Cl)([Cl:28])=O.S(=O)=O>C1C=CC=CC=1>[CH2:1]([Cl:28])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
67 gms of oleyl alcohol was dissolved in 75 mls of benzene, 0.15 ml of pyridine were added. The solution was cooled to 0° C. and 46 gms of thionyl chloride was added over 5 minutes with stirring. The solution was heated to reflux temperature for 10 minutes until all sulphur dioxide evolution ceased. It was cooled and extracted with 150 ml of 10% saline solution then with 50 ml of 10% sodium carbonate solution and finally with 100 ml of 10% saline solution. The organic layer was dried over sodium sulphate, evaporated and distilled. The product distilled at 166°-169° C., at 3 torr and yielded 58 gms of oleyl chloride.
Workup
- temperatureThe solution was heated
- temperatureIt was cooled
- extractionextracted with 150 ml of 10% saline solution
- dry with materialThe organic layer was dried over sodium sulphate
- customevaporated
- distillationdistilled
- distillationThe product distilled at 166°-169° C., at 3 torr
Sources & evidence
- ORD record
- ord-0e9fd8955d63485faf87aea23e1303c4
- Source dataset
- uspto-grants-1980_07
- Patent number
- US04212830
Reaction notes
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