Water → 5-Benzyloxymethyl-2,2-dimethyl-5-ethyl-1,3-dioxane

HRID 2372420

Reaction equation

HRID 2372420 reaction equation
[CH3:1][C:2]1([CH3:12])[O:7][CH2:6][C:5]([CH2:10][CH3:11])([CH2:8][OH:9])[CH2:4][O:3]1.[H-].[Na+].[CH2:15](Cl)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.O>O1CCCC1>[CH2:15]([O:9][CH2:8][C:5]1([CH2:10][CH3:11])[CH2:4][O:3][C:2]([CH3:12])([CH3:1])[O:7][CH2:6]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7503Benzyl ChlorideHCID 24758Sodium hydrideHCID 118161521,3-Dioxane-5-methanol, 5-ethyl-2,2-dimethyl-

Product 1

HCID 199044005-Benzyloxymethyl-2,2-dimethyl-5-ethyl-1,3-dioxane

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2,2-Dimethyl-5-ethyl-5-hydroxymethyl-1,3-dioxane (10 g.) was added to a stirred suspension of sodium hydride (2.4 g., 50% dispersion in oil) in dry tetrahydrofuran (80 ml.) The mixture was refluxed with stirring for one hour. Benzyl chloride (9.2 ml.) was added and the mixture was refluxed with stirring for three hours. the mixture was poured into water and the aqueous mixture was extracted with ether. The ethereal extract was washed with water, dried over anhydrous magnesium sulphate and evaporated in vacuo. 5-Benzyloxymethyl-2,2-dimethyl-5-ethyl-1,3-dioxane was obtained as a pale brown oil (15 g.) and was used without further purification.

Workup

  1. temperaturewas refluxed
  2. temperaturethe mixture was refluxed
  3. stirringwith stirring for three hours
  4. extractionthe aqueous mixture was extracted with ether
  5. extractionThe ethereal extract
  6. washwas washed with water
  7. dry with materialdried over anhydrous magnesium sulphate
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-4df1e1f96fc046e49e70467d5c965774
Source dataset
uspto-grants-1992_03
Patent number
US05098929

Linked notes

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