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

HRID 372509Notes

Reaction equation

HRID 372509 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

5

Reactant 3

HCID 80803,4-dihydro-2H-pyranHCID 14798Sodium HydroxideHCID 203860821-Chlorononan-4-ol

Product 1

HCID 203276861-Chloro-4-(2-tetrahydropyranyloxy)nonane

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidCatalyst

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.

Workup

  1. customA slight exothermic reaction
  2. customto come to room temperature
  3. distillationthe reaction is distilled in vacuo
  4. customboiling 96°-102°
  5. distillationUpon redistillation a boiling point of 90°-92°/0.1 mm
  6. customis obtained

Sources & evidence

ORD record
ord-63d8953766aa4f0cbfe1a08ea1c5c844
Source dataset
uspto-grants-1978_05
Patent number
US04091107

Reaction notes

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