Diethyl Ether → (4-Methylbicyclo[2.2.2]octan-1-yl)methanol

HRID 461990Notes

Reaction equation

HRID 461990 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C(OCC)C.[CH3:12][C:13]12[CH2:20][CH2:19][C:16]([C:21](O)=[O:22])([CH2:17][CH2:18]1)[CH2:15][CH2:14]2.O1CCCC1>O.C(OCC)(=O)C>[OH:22][CH2:21][C:16]12[CH2:17][CH2:18][C:13]([CH3:12])([CH2:20][CH2:19]1)[CH2:14][CH2:15]2

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 8028TetrahydrofuranHCID 136544Bicyclo(2.2.2)octane-1-carboxylic acid, 4-methyl-HCID 21226445Aluminium lithium hydride2×

Product 1

HCID 13227648(4-Methylbicyclo[2.2.2]octan-1-yl)methanol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

0.0952 Mole of lithium aluminum hydride is dissolved in 200 ml. of anhydrous diethyl ether, under nitrogen, and cooled to 0° C. 0.0952 Mole of 4-methylbicyclo[2.2.2]oct-1-yl carboxylic acid in 100 ml. of tetrahydrofuran is added dropwise, then the mixture stirred for 30 minutes. Excess lithium aluminum hydride is decomposed by the cautious addition of ethyl acetate, followed by the careful addition of 10 ml. of water. The mixture is then filtered and the filtrate washed with ethyl ether, then dried over anhydrous magnesium sulfate and filtered. The solvent is then evaporated from the filtrate, under vacuum, affording 1-(hydroxymethyl)-4-methylbicyclo[2.2.2]octane.

Workup

  1. additionfollowed by the careful addition of 10 ml
  2. filtrationThe mixture is then filtered
  3. washthe filtrate washed with ethyl ether
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customThe solvent is then evaporated from the filtrate, under vacuum

Sources & evidence

ORD record
ord-f0bf4585fc164ba4b2f62705de1a3733
Source dataset
uspto-grants-1977_12
Patent number
US04064258

Reaction notes

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