Diethyl Ether → 2,2-Dimethyl-1,3-dioxan-5-ol

HRID 31602Notes

Reaction equation

HRID 31602 reaction equation
C(OCC)C.[CH3:6][C:7]1([CH3:14])[O:12][CH2:11][C:10](=[O:13])[CH2:9][O:8]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>O>[CH3:6][C:7]1([CH3:14])[O:12][CH2:11][CH:10]([OH:13])[CH2:9][O:8]1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 14798Sodium HydroxideHCID 27331412,2-Dimethyl-1,3-dioxan-5-oneHCID 21226445Aluminium lithium hydride

Product 1

HCID 110298842,2-Dimethyl-1,3-dioxan-5-olYield 93.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a diethyl ether (150 ml) solution of 2,2-dimethyl-1,3-dioxan-5-one (15 g, 0.115 mol), lithium aluminum hydride (4.38 g, 0.115 mol) was added at 0 to 8° C. for one hour in a nitrogen atmosphere. To the reaction mixture, water (4.2 ml), a 5N aqueous sodium hydroxide solution (4.2 ml), and water (12.8 ml) were sequentially added dropwise at 0 to 10° C. The mixture was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to obtain the title compound (14.2 g, 93.4%) as a colorless oil.

Workup

  1. dry with materialThe mixture was dried over anhydrous sodium sulfate
  2. filtrationfiltered
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b7f23c757586434598dcb08ac7ddb4a1
Source dataset
uspto-grants-2008_09
Patent number
US07425634B2

Reaction notes

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