Sodium Hydroxide → 2-(2-Ethyl-1,3-dioxolan-2-yl)ethan-1-ol

HRID 31655Notes

Reaction equation

HRID 31655 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O:9][C:10](=O)[CH2:11][C:12]1([CH2:17][CH3:18])[O:16][CH2:15][CH2:14][O:13]1)C.[OH-].[Na+].S([O-])([O-])(=O)=O.[Mg+2]>O.O1CCCC1>[CH2:17]([C:12]1([CH2:11][CH2:10][OH:9])[O:16][CH2:15][CH2:14][O:13]1)[CH3:18]

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 24083Sulfuric acid magnesium salt (1:1)HCID 14244230Ethyl 2-(2-ethyl-1,3-dioxolan-2-yl)acetateHCID 21226445Aluminium lithium hydride

Product 1

HCID 139403682-(2-Ethyl-1,3-dioxolan-2-yl)ethan-1-olYield 92.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a tetrahydrofuran (50 ml) suspension of lithium aluminum hydride (800 mg, 21.1 mmol), ethyl(2-ethyl-1,3-dioxolan-2-yl)acetate (3.85 g, 20.5 mmol) was added under ice-cool. The mixture was stirred at room temperature for one hour and 30 minutes and cooled on ice. Thereafter, water (0.8 ml), a 15% aqueous sodium hydroxide solution (0.8 ml), and water (2.4 ml) were sequentially added to the mixture under ice cool. Magnesium sulfate was added to the mixture and filtrated through silica gel. The filtrate was concentrated under reduced pressure to obtain the title compound (2.76 g, 92.1%) as an oil.

Workup

  1. additionwas added under ice-
  2. temperaturecool
  3. temperaturecooled on ice
  4. temperaturecool
  5. filtrationfiltrated through silica gel
  6. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-6a0249feb7ae450a8aec182a77b8221c
Source dataset
uspto-grants-2008_09
Patent number
US07425634B2

Reaction notes

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