Sodium Bicarbonate → 4,4-Ethylenedioxy-3-methyl-1-butanol

HRID 27354Notes

Reaction equation

HRID 27354 reaction equation
[CH2:1]1[CH2:12][O:11][CH:3]([CH:4]([CH3:10])[CH2:5][C:6](OC)=[O:7])[O:2]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].C(=O)(O)[O-].[Na+]>CCOCC>[CH2:1]1[CH2:12][O:11][CH:3]([CH:4]([CH3:10])[CH2:5][CH2:6][OH:7])[O:2]1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 20305753Methyl 4,4-ethylenedioxy-3-methyl-butanoateHCID 21226445Aluminium lithium hydride

Product 1

HCID 203057524,4-Ethylenedioxy-3-methyl-1-butanolYield 28.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of methyl 4,4-ethylenedioxy-3-methylbutanoate (63.2 g) in ether (200 ml) is added dropwise to a mixture of lithium aluminum hydride (13.8 g, 0.363 m) in ether (500 ml) at 0° C. under nitrogen. The resulting mixture is stirred for 2 hr., treated with 5% sodium bicarbonate solution (100 ml), allowed to warm to room temperature and filtered. The filtrate is dried (Na2SO4) and the solvent is evaporated in vacuo to give the crude product (26 g). This material is further purified by column chromatography on silica gel (300 g, 20% ethyl acetate in hexane) to give 4,4-ethylenedioxy-3-methyl-1-butanol as a colorless liquid (14.9 g).

Workup

  1. filtrationfiltered
  2. dry with materialThe filtrate is dried (Na2SO4)
  3. customthe solvent is evaporated in vacuo
  4. customto give the crude product (26 g)
  5. customThis material is further purified by column chromatography on silica gel (300 g, 20% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-eb178ed36c2c47eea34d97508000c9b4
Source dataset
uspto-grants-1980_09
Patent number
US04221717

Reaction notes

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