Ethyl Acetate → HCID 13071121, compound

HRID 267256Notes

Reaction equation

HRID 267256 reaction equation
[CH:1]12[CH2:11][CH:6]3[CH2:7][CH:8]([O:10][CH:4]([O:5]3)[C:3](=[O:12])[O:2]1)[CH2:9]2.[H-].[Al+3].[Li+].[H-].[H-].[H-].C(OCC)(=O)C>COCCOC>[OH:12][CH2:3][CH:4]1[O:10][CH:8]2[CH2:7][CH:6]([CH2:11][CH:1]([OH:2])[CH2:9]2)[O:5]1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 15629417HCID 15629417, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 13071121HCID 13071121, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Procedure

A solution of 8.50 g (0.05 mols) of 2,5,11-trioxatricyclo[4,3,1,14,8 ]undecan-3-one of the formula Ia in 90 ml of ethylene glycol dimethyl ether is added dropwise within 15 minutes, while stirring and cooling with ice, to a suspension of 2.0 g (0.05 mols) of lithium aluminium hydride in 60 ml of ethylene glycol dimethyl ether. The reaction mixture is boiled for 15 minutes under reflux, cooled to room temperature and carefully treated with 10 ml of ethyl acetate to destroy excess lithium aluminium hydride. Then, while stirring, 2.0 ml of water, 2.0 ml of 15% sodium hydroxide solution, and finally 6 ml of water, are added to the reaction mixture. The precipitated salts are filtered off, stirred with 100 ml of methylene chloride and filtered again. The combined filtrates are concentrated in a water jet vacuum. The crystalline residue is recrystallised from methylene chloride to give 3-hydroxymethyl-2,4-dioxabicyclo[3,3,1]nonan-7-ol of the formula IIa ##SPC9##

Workup

  1. temperatureunder reflux
  2. customto destroy excess lithium aluminium hydride
  3. stirringThen, while stirring
  4. addition2.0 ml of water, 2.0 ml of 15% sodium hydroxide solution, and finally 6 ml of water, are added to the reaction mixture
  5. filtrationThe precipitated salts are filtered off
  6. stirringstirred with 100 ml of methylene chloride
  7. filtrationfiltered again
  8. concentrationThe combined filtrates are concentrated in a water jet vacuum
  9. customThe crystalline residue is recrystallised from methylene chloride

Sources & evidence

ORD record
ord-0547b67c91d544dfa79404886a49b01b
Source dataset
uspto-grants-1976_03
Patent number
US03941813

Reaction notes

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