1-Bromooctane → 3-Octoxymethyl-3-methyloxetane

HRID 34965

Reaction equation

HRID 34965 reaction equation
[OH:1][CH2:2][C:3]1([CH3:7])[CH2:6][O:5][CH2:4]1.[Na].Br[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]>O1CCOCC1>[CH2:10]([O:1][CH2:2][C:3]1([CH3:7])[CH2:6][O:5][CH2:4]1)[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]

Participants

5

Reactant 3

HCID 81401-BromooctaneHCID 1378373-Methyl-3-oxetanemethanolHCID 5360545Sodium2×

Product 1

HCID 144346343-Octoxymethyl-3-methyloxetaneYield 58%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Into a 5 liter, three-neck flask, fitted with a stirrer, reflux condenser, and nitrogen inlet tube, were placed 245 g (2.4 mole) of 3-hydroxymethyl-3-methyloxetane and 3000 ml of p-dioxane. To this solution 47 g (2 mole) of solid sodium metal was added, and the pot temperature was raised to reflux. Heat was maintained until all of the sodium had dissolved. 400 g (2 mole) of 1-bromooctane was added, and the reflux was resumed for 3 days. The mixture was cooled to room temperature, and the solid sodium bromide was filtered off using celite. The solvent was removed by evaporation and the product was distilled at 80° C. and 0.3-mm pressure. Redistillation from calcium hydride gave 231 g of polymerizable monomer, representing a 58 percent yield.

Workup

  1. customInto a 5 liter, three-neck flask, fitted with a stirrer
  2. temperaturereflux condenser, and nitrogen inlet tube
  3. temperaturethe pot temperature was raised
  4. temperatureto reflux
  5. temperatureHeat
  6. dissolutionhad dissolved
  7. filtrationthe solid sodium bromide was filtered off
  8. customThe solvent was removed by evaporation
  9. distillationthe product was distilled at 80° C.
  10. distillationRedistillation from calcium hydride

Sources & evidence

ORD record
ord-101502ab77eb40c4a13d0614e6644675
Source dataset
uspto-grants-1988_08
Patent number
US04764586

Linked notes

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