Sodium Hydroxide → HCID 21461393, compound

HRID 1941517Notes

Reaction equation

HRID 1941517 reaction equation
[CH3:1][C:2]12[C:8]([CH3:10])([CH3:9])[CH:5]([CH2:6][CH2:7]1)[CH2:4][C:3]2([CH2:12][C:13]1([CH3:16])[CH2:15][O:14]1)[OH:11].[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+].[O-]S([O-])(=O)=O.[Mg+2]>C(OCC)C>[OH:14][C:13]([CH3:16])([CH3:15])[CH2:12][C:3]1([OH:11])[CH2:4][CH:5]2[C:8]([CH3:9])([CH3:10])[C:2]1([CH3:1])[CH2:7][CH2:6]2

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 24083Sulfuric acid magnesium salt (1:1)HCID 21226445Aluminium lithium hydrideHCID 21461390HCID 21461390, compound

Product 1

HCID 21461393HCID 21461393, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 30.9 g (~0.14 mol) of crude (1RS,2SR,4RS)-1,7,7-trimethyl-2-(2-methyl-oxiranylmethyl)bicyclo[2.2.1]heptan-2-ol in 100 ml of anhydrous diethyl ether was added dropwise to 11.0 g (0.29 mol) of lithium aluminum hydride suspended in 300 ml of the same solvent under reflux, and under nitrogen. The reaction mixture was stirred overnight at room temperature and treated with 60 ml of 2M sodium hydroxide solution. The white precipitate was filtered out, washed with diethyl ether and the combined organic phases were washed with 2×200 ml of water and 200 ml of brine. After drying (MgSO4) and evaporation of solvent the crude (1RS,2SR,4RS)-2-(2-hydroxy-2-methylpropyl)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol (29.0 g of white waxy solid; two step yield 92%) was used in the next steps without further purification.

Workup

  1. temperatureunder reflux
  2. filtrationThe white precipitate was filtered out
  3. washwashed with diethyl ether
  4. washthe combined organic phases were washed with 2×200 ml of water and 200 ml of brine
  5. customAfter drying

Sources & evidence

ORD record
ord-eb922cde6dcf462aad27f8b2d3599be7
Source dataset
uspto-grants-1997_12
Patent number
US05703250

Reaction notes

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