Hydride → 4,4-Ethylenedioxy-3-methyl-1-butanol

HRID 1732279Notes

Reaction equation

HRID 1732279 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.[Li].[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

6

Reactant 4

HCID 166653HydrideHCID 516892Sodium BicarbonateHCID 3028194LithiumHCID 20305753Methyl 4,4-ethylenedioxy-3-methyl-butanoate

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-methyl-butanoate (63.2 g) in ether (200 ml) is added dropwise to a mixture of lithium alumnium hydride (13.8 g, 0.363 m) in ether (500 ml) at 0° C. under nitrogen. The resulting mixture is stirred for 2 hours, 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-c7a6b375c5794b85b18ca5f0bb586559
Source dataset
uspto-grants-1980_12
Patent number
US04237054

Reaction notes

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