Adamantanone → 2-Adamantanol

HRID 1088485Notes

Reaction equation

HRID 1088485 reaction equation
[CH:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[C:2]1=[O:11])[CH2:8]2.[H-].[Al+3].[Li+].[H-].[H-].[H-]>CCOCC>[CH:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH:2]1[OH:11])[CH2:8]2

Participants

4

Reactant 2

HCID 64151AdamantanoneHCID 21226445Aluminium lithium hydride

Product 1

HCID 641492-Adamantanol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
25 °C

Procedure

Dissolved in 300 ml of ether was 30.0 g (0.20 mole) of 2 -adamantanon and 7.3 g (0.19 mole) of lithium aluminum hydride suspended in 150 ml of ether was added. The mixture was stirred for 2 hours at room temperature (25° C). After 2-N-HCl was added to make it acidic and the water layer was extracted with dichloromethane, it was washed together with the ether layer and dried with sodium sulfate. The solvent was removed by evaporation at reduced pressure to obtain white powder. The test results were as follows:

Workup

  1. additionwas added
  2. extractionthe water layer was extracted with dichloromethane, it
  3. washwas washed together with the ether layer
  4. dry with materialdried with sodium sulfate
  5. customThe solvent was removed by evaporation at reduced pressure
  6. customto obtain white powder
  7. customThe test results

Sources & evidence

ORD record
ord-700b86621dff4006b20a4ff884d53f54
Source dataset
uspto-grants-1990_10
Patent number
US04962225

Reaction notes

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