Water → HCID 21995935, compound

HRID 1978748Notes

Reaction equation

HRID 1978748 reaction equation
[Cl:1][CH2:2][C:3]([CH3:7])([CH3:6])[CH2:4][OH:5].[O:8]1[CH:13]=[CH:12][CH2:11][CH2:10][CH2:9]1.O>C(OCC)(=O)C.C12(CS(O)(=O)=O)C(C)(C)C(CC1)CC2=O>[Cl:1][CH2:2][C:3]([CH3:7])([CH3:6])[CH2:4][O:5][CH:9]1[CH2:10][CH2:11][CH2:12][CH2:13][O:8]1

Participants

6

Reactant 3

HCID 962WaterHCID 80803,4-dihydro-2H-pyranHCID 834071-Propanol, 3-chloro-2,2-dimethyl-

Product 1

HCID 21995935HCID 21995935, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-CatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-chloro-2,2-dimethylpropanol (5.0 g) and 2,3-dihydropyran (4.12 g) in ethyl acetate (20 ml) was added camphor sulfonic acid (57 mg), and the mixture was stirred for 19 hours. To the mixture was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with O.1N sodium hydroxide solution and saturated brine, and dried with magnesium sulfate. The solvent was evaporated under reduced pressure and distilled under reduced pressure (2 mmHg, 108° C.) to give colorless oil of 2-(3-chloro-2,2-dimethylpropoxy)tetrahydropyran (6.07 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with O
  3. dry with material1N sodium hydroxide solution and saturated brine, and dried with magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. distillationdistilled under reduced pressure (2 mmHg, 108° C.)

Sources & evidence

ORD record
ord-d7a5ef9066144f478b1604dba4cf9080
Source dataset
uspto-grants-2001_05
Patent number
US06235771B1

Reaction notes

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