Potassium Hydroxide → HCID 19904422, compound

HRID 2372419Notes

Reaction equation

HRID 2372419 reaction equation
[C:1]([C:6]1([C:13](OCC)=[O:14])[CH2:11][CH2:10][CH2:9][CH2:8][C:7]1=[O:12])(OCC)=[O:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[K+].P([O-])([O-])(O)=O.[K+].[K+].P([O-])(O)(O)=O.[K+]>CCOCC.O>[OH:14][CH2:13][C:6]1([CH2:1][OH:2])[CH2:11][CH2:10][CH2:9][CH2:8][CH:7]1[OH:12]

Participants

8

Reactant 5

HCID 14797Potassium HydroxideHCID 24450Potassium Phosphate, DibasicHCID 224023diethyl 2-oxocyclohexane-1,1-dicarboxylateHCID 516951Monobasic potassium phosphateHCID 21226445Aluminium lithium hydride

Product 1

HCID 19904422HCID 19904422, compoundYield 60.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 2,2-dicarbethoxycyclohexanone (3.0 g.) in dry ether (15 ml.) was added dropwise to a stirred suspension of lithium aluminium hydride (1.4 g.) in dry ether (50 ml.) at 0°, under nitrogen. The mixture was refluxed, with stirring, for six hours. Potassium hydroxide (6 g.) in water (100 ml) was added to the stirred mixture. Dipotassium hydrogen phosphate (4.2 g.) and potassium dihydrogen phosphate (3.3 g.) in water (50 ml.) was added. Ether was removed by passing a current of nitrogen through the mixture. The resultant slurry was acidified with glacial acetic acid and the solid was filtered off. The filtrate was evaporated in vacuo. The residue was extracted with acetone and the solution was evaporated in vacuo. 2,2Di-(hydroxymethyl)-cyclohexanol (1.2 g.) was obtained as a pale yellow oil.

Workup

  1. temperatureThe mixture was refluxed
  2. customEther was removed
  3. filtrationthe solid was filtered off
  4. customThe filtrate was evaporated in vacuo
  5. extractionThe residue was extracted with acetone
  6. customthe solution was evaporated in vacuo

Sources & evidence

ORD record
ord-b58d505661ee43bc907e035160e47acb
Source dataset
uspto-grants-1992_03
Patent number
US05098929

Reaction notes

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