Water → (2,2-Dimethyl-1,3-dioxan-5-yl)methanol

HRID 1651493Notes

Reaction equation

HRID 1651493 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][C:8]1([CH3:19])[O:13][CH2:12][CH:11]([C:14](OCC)=[O:15])[CH2:10][O:9]1.O.[OH-].[Na+]>CCOCC>[CH3:7][C:8]1([CH3:19])[O:13][CH2:12][CH:11]([CH2:14][OH:15])[CH2:10][O:9]1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 11019611Ethyl 2,2-dimethyl-1,3-dioxane-5-carboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 3584869(2,2-Dimethyl-1,3-dioxan-5-yl)methanolYield 86.8%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Lithium aluminum hydride (80 g) is stirred in ether (2000 ml) while the product of Example 3 (230 g) in ether (250 ml) is added dropwise. When the addition is complete the mixture is stirred an additional 16 hours. The reaction mixture is decomposed by careful addition of water (80 ml) followed by 15% aqueous sodium hydroxide (80 ml) and additional water (240 ml). The resulting suspension is filtered, the filter cake washed with ethanol and ether and the combined filtrates evaporated to give a residue. Distillation of the residue gives the title product (155 g) (81%) B.P. 75° C. (0.05 mm).

Workup

  1. additionis added dropwise
  2. additionWhen the addition
  3. filtrationThe resulting suspension is filtered
  4. washthe filter cake washed with ethanol and ether
  5. customthe combined filtrates evaporated
  6. customto give a residue
  7. distillationDistillation of the residue

Sources & evidence

ORD record
ord-25b08a7ad8e14fda86bf7cbb0aa9d6d6
Source dataset
uspto-grants-1990_05
Patent number
US04929291

Reaction notes

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