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

HRID 1645599Notes

Reaction equation

HRID 1645599 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([C:9]1([CH2:14][C:15](OCC)=[O:16])[O:13][CH2:12][CH2:11][O:10]1)[CH3:8].[OH-].[Na+].S([O-])([O-])(=O)=O.[Mg+2]>O.O1CCCC1>[CH2:7]([C:9]1([CH2:14][CH2:15][OH:16])[O:13][CH2:12][CH2:11][O:10]1)[CH3:8]

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-deb99deb18ad4d5aa48a6c18b78c0a1f
Source dataset
uspto-grants-2012_02
Patent number
US08124780B2

Reaction notes

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