Ammonia → 5-Cyclohexyl-2,2-dimethyl-5-hydroxymethyl-1,3-dioxane

HRID 2372414Notes

Reaction equation

HRID 2372414 reaction equation
C([O:8][CH2:9][C:10]1([CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)[CH2:15][O:14][C:13]([CH3:17])([CH3:16])[O:12][CH2:11]1)C1C=CC=CC=1.N.[Na].[Cl-].[NH4+]>CCOCC>[CH:18]1([C:10]2([CH2:9][OH:8])[CH2:15][O:14][C:13]([CH3:16])([CH3:17])[O:12][CH2:11]2)[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 25517Ammonium ChlorideHCID 5360545SodiumHCID 199044385-Benzyloxymethyl-5-cyclohexyl-2,2-dimethyl-1,3-dioxane

Product 1

HCID 199044325-Cyclohexyl-2,2-dimethyl-5-hydroxymethyl-1,3-dioxane

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

5-Benzyloxymethyl-5-cyclohexyl-2,2-dimethyl-1,3-dioxane (3.0 g.) in dry ether (10 ml.) was added to liquid ammonia (100 ml.) at -70°. Sodium (0.5 g.) was added to the stirred solution. Stirring was maintained at -70°, for one hour. The mixture was then allowed to warm up to -30° and solid ammonium chloride (2.0 g.) was added. The ammonia was removed from the reaction mixture under a current of nitrogen. Water was added and the aqueous mixture was extracted with diethyl ether. The ethereal extracts were washed with water, dried over anhydrous magnesium sulphate and evaporated in vacuo. 5-Cyclohexyl-2,2-dimethyl-5-hydroxymethyl-1,3-dioxane was obtained as a cream solid (2.15 g.) and was used without further purification.

Workup

  1. temperaturewas maintained at -70°, for one hour
  2. temperatureto warm up to -30°
  3. customThe ammonia was removed from the reaction mixture under a current of nitrogen
  4. additionWater was added
  5. extractionthe aqueous mixture was extracted with diethyl ether
  6. washThe ethereal extracts were washed with water
  7. dry with materialdried over anhydrous magnesium sulphate
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-7f5b72d69f7e4700850cf9967322b03f
Source dataset
uspto-grants-1992_03
Patent number
US05098929

Reaction notes

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