3,4-dihydro-2H-pyran → 1-Chloro-4-(2-tetrahydropyranyloxy)nonane

Reaction equation

[Cl:1][CH2:2][CH2:3][CH2:4][CH:5]([OH:11])[CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[O:12]1[CH:17]=[CH:16][CH2:15][CH2:14][CH2:13]1.[OH-].[Na+]>Cl>[Cl:1][CH2:2][CH2:3][CH2:4][CH:5]([O:11][CH:13]1[CH2:14][CH2:15][CH2:16][CH2:17][O:12]1)[CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

Participants

Procedure

To a stirred solution of 1-chloro-4-hydroxynonane (Example A, Step 2) (11.0 g., 0.062 mole) and dihydropyrane (5.2 g., 0.062 mole) cooled in an ice bath is added 5 drops of hydrochloric acid (conc.). A slight exothermic reaction is noted and when this is complete the reaction is allowed to come to room temperature, then stand for 2 hours. At the end of this period several pellets of sodium hydroxide are added and the reaction is distilled in vacuo. The yield of 1-chloro-4-(2-tetrahydropyranyloxy)nonane is 12.5 g. (77%), boiling 96°-102°/0.1 mm. Upon redistillation a boiling point of 90°-92°/0.1 mm. is obtained.