3,4-dihydro-2H-pyran → 2-(6-Chlorohexyloxy)tetrahydro-2H-pyran

HRID 2371558

Reaction equation

HRID 2371558 reaction equation
[Cl:1][CH:2](O)[CH2:3][CH2:4][CH2:5][CH2:6]C.[O:9]1[CH:14]=[CH:13][CH2:12][CH2:11][CH2:10]1.[C:15](=[O:18])(O)[O-].[Na+]>C(Cl)Cl>[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:15][O:18][CH:14]1[CH2:13][CH2:12][CH2:11][CH2:10][O:9]1

Participants

5

Reactant 3

HCID 80803,4-dihydro-2H-pyranHCID 516892Sodium BicarbonateHCID 12768704Chlorohexanol

Product 1

HCID 3298032-(6-Chlorohexyloxy)tetrahydro-2H-pyran

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 14.3-7g of 6 chloro-1-hexanol and 10.39 g of dihydropyran in 30 ml of methylene chloride was added 0.95 g of tosic acid monohydrate, and the mixture was stirred at room temperature for 18 hours, poured into 50 ml of a saturated sodium bicarbonate aqueous solution, stirred for 10 minutes and extracted three times with 100 ml of chloroform. The extracts were combined, washed with a saturated sodium bicarbonate aqueous solution and a saturated sodium chloride aqueous solution, dried over magnesium sulfate, concentrated under a reduced pressure and dried in vacuo. The orange-colored oil thus obtained was vacuum-distilled to obtain 17.43 g of 2-(6-chlorohexyloxy)tetrahydropyran as a colorless oil.

Workup

  1. stirringstirred for 10 minutes
  2. extractionextracted three times with 100 ml of chloroform
  3. washwashed with a saturated sodium bicarbonate aqueous solution
  4. dry with materiala saturated sodium chloride aqueous solution, dried over magnesium sulfate
  5. concentrationconcentrated under a reduced pressure
  6. customdried in vacuo
  7. customThe orange-colored oil thus obtained
  8. distillationwas vacuum-distilled

Sources & evidence

ORD record
ord-4cb1d50d1f4840a694eef5b84eff9b58
Source dataset
uspto-grants-1992_03
Patent number
US05093370

Linked notes

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