Hexane → 3-{[(6-Bromohexyl)oxy]methyl}-3-methyloxetane

HRID 433049Notes

Reaction equation

HRID 433049 reaction equation
[OH-].[Na+].CCCCCC.[OH:9][CH2:10][C:11]1([CH3:15])[CH2:14][O:13][CH2:12]1.[Br:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]Br>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)(=O)C.O>[Br:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][O:9][CH2:10][C:11]1([CH3:15])[CH2:14][O:13][CH2:12]1

Participants

8

Reactant 4

HCID 8058HexaneHCID 123681,6-DibromohexaneHCID 14798Sodium HydroxideHCID 1378373-Methyl-3-oxetanemethanol

Product 1

HCID 144346313-{[(6-Bromohexyl)oxy]methyl}-3-methyloxetane

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A 50% aqueous sodium hydroxide solution (65.0 g), tetrabutylammonium bromide (0.8 g, 2.5 mmol) and hexane (200 ml) were cooled with stirring in an ice bath. Compound 29 (16.32 g, 0.16 mol) and 1,6-dibromohexane (30) (100.00 g, 0.41 mol) were added and the reaction was left stirring until it reached room temperature; the reaction mixture was then heated under reflux for 3 h and then cooled to below 5° C. Water (300 ml) was added and the organic layer was retained and dried (Na2SO4). The drying agent was filtered off and the solvent was removed in vacuo. The resulting oil was purified by column chromatography [dichloromethane:hexane (1:6), to remove excess dibromohexane, dichloromethane, to isolate the product and then ethyl acetate to obtain the doubly reacted product) on silica.

Workup

  1. waitthe reaction was left
  2. stirringstirring until it
  3. customreached room temperature
  4. temperaturethe reaction mixture was then heated
  5. temperatureunder reflux for 3 h
  6. temperaturecooled to below 5° C
  7. dry with materialdried (Na2SO4)
  8. filtrationThe drying agent was filtered off
  9. customthe solvent was removed in vacuo
  10. customThe resulting oil was purified by column chromatography [dichloromethane:hexane (1:6)
  11. customto remove excess dibromohexane, dichloromethane
  12. customto isolate the product

Sources & evidence

ORD record
ord-b48b52a0d17545c88ee472451546d2c7
Source dataset
uspto-grants-2003_12
Patent number
US06666989B1

Reaction notes

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