1-Hexanol → (R)-(+)-2,3-EPOXYPROPYL HEXYL ETHER

HRID 1720843Notes

Reaction equation

HRID 1720843 reaction equation
[CH2:1]([OH:7])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[OH-].[Na+].[CH2:10]([C@@H:12]1[O:14][CH2:13]1)Cl>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.O>[CH2:1]([O:7][CH2:10][C@@H:12]1[O:14][CH2:13]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

6

Reactant 3

HCID 81031-HexanolHCID 14798Sodium HydroxideHCID 2734062(-)-Epichlorohydrin

Product 1

HCID 36691064(R)-(+)-2,3-EPOXYPROPYL HEXYL ETHER

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 962WaterSolvent

Procedure

6 ml of n-hexanol was added dropwise to a mixture of 40 g of sodium hydroxide, 24 g of (R)-epichlorohydrin as used in Synthetic Example 1 and 400 mg of tetra-butylammonium hydrogensulfate under cooling at 20° to 25° C. The reaction mixture was stirred for 3 hours at the same temperature, to which water was added. The product was extracted with ether, and the extract was purified by vacuum distillation to obtain 3.35 g of (R)-n-hexylglycidyl ether.

Workup

  1. temperatureunder cooling at 20° to 25° C
  2. additionwas added
  3. extractionThe product was extracted with ether
  4. distillationthe extract was purified by vacuum distillation

Sources & evidence

ORD record
ord-bbe72e1199e842d0a468806b6fce0083
Source dataset
uspto-grants-1996_04
Patent number
US05507975

Reaction notes

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