Water → Ethanol, 2-(1,4-benzodioxan-2-yl)-

HRID 1196022Notes

Reaction equation

HRID 1196022 reaction equation
C[O:2][C:3]([CH2:5][CH:6]1[O:11][C:10]2[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=2[O:8][CH2:7]1)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1.C(OCC)C>[OH:2][CH2:3][CH2:5][CH:6]1[O:11][C:10]2[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=2[O:8][CH2:7]1

Participants

7

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 13279114Methyl (2,3-dihydro-1,4-benzodioxin-2-yl)acetateHCID 21226445Aluminium lithium hydride

Product 1

HCID 98334Ethanol, 2-(1,4-benzodioxan-2-yl)-Yield 91.6%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

At room temperature and while stirring, a solution of 15.61 g (75 mmol) of 2-methoxycarbonylmethylbenzo-1,4-dioxan in 120 ml of absolute tetrahydrofuran is added dropwise within a period of 30 minutes to a suspension of 2.85 g (75 mmol) of lithium aluminium hydride in 120 ml of absolute diethyl ether. The reaction mixture is stirred for a further 2 hours at room temperature. It is then carefully decomposed with 2.85 ml of water, 2.85 ml of sodium hydroxide solution (15% strength) and 8.55 ml of water. The precipitate formed is filtered off with suction and the filtrate is concentrated by evaporation in vacuo. The oily residue is dissolved in diethyl ether. The solution is washed thoroughly with water, dried over sodium sulphate and concentrated by evaporation in vacuo. 12.37 g (91.6%) of 2-(2-hydroxyethyl)-benzo-1,4-dioxan are obtained in the form of a colourless oil.

Workup

  1. stirringThe reaction mixture is stirred for a further 2 hours at room temperature
  2. customThe precipitate formed
  3. filtrationis filtered off with suction
  4. concentrationthe filtrate is concentrated by evaporation in vacuo
  5. dissolutionThe oily residue is dissolved in diethyl ether
  6. washThe solution is washed thoroughly with water
  7. dry with materialdried over sodium sulphate
  8. concentrationconcentrated by evaporation in vacuo

Sources & evidence

ORD record
ord-0df147c084204ce3a3121a39b437749b
Source dataset
uspto-grants-1992_05
Patent number
US05112855

Reaction notes

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