Potassium Hydroxide → 3,3-Di-(hydroxymethyl)-hexan-1-ol

HRID 704134Notes

Reaction equation

HRID 704134 reaction equation
C([O:3][C:4]([C:6]([CH2:18][CH2:19][CH3:20])([CH2:12][C:13](OCC)=[O:14])[C:7](OCC)=[O:8])=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[K+].P([O-])(O)(O)=O.[K+].P([O-])([O-])(O)=O.[K+].[K+]>CCOCC.O.C(O)(=O)C>[OH:3][CH2:4][C:6]([CH2:7][OH:8])([CH2:18][CH2:19][CH3:20])[CH2:12][CH2:13][OH:14]

Participants

9

Reactant 5

HCID 14797Potassium HydroxideHCID 24450Potassium Phosphate, DibasicHCID 516951Monobasic potassium phosphateHCID 20075591Diethyl 2-prop-1-yl-2-ethoxycarbonylsuccinateHCID 21226445Aluminium lithium hydride

Product 1

HCID 218851593,3-Di-(hydroxymethyl)-hexan-1-ol

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×

Procedure

Diethyl 2-ethoxycarbonyl-2-n-propyl-succinate (55.8 g) in dry ether (50 ml.) was added slowly to a stirred suspension of lithium aluminium hydride (14.7 g.) in dry ether (150 ml.) at 0°, under a current of nitrogen. The mixture was stirred at room temperature for three hours and then refluxed, with stirring for four hours. A solution of potassium hydroxide (30.0 g.), potassium dihydrogen phosphate (22.0 g.) and potassium monohydrogen phosphate (22.0 g.) in water (200 ml.) was added to the cooled reaction mixture. The pH was adjusted to 5.0 with glacial acetic acid. The solid was removed by filtration and washed with water (40 ml.) The combined filtrates and washings were evaporated in vacuo. The residue was washed with acetone (3×100 ml). The acetone washings were evaporated in vacuo. The residue was washed with chloroform (3×100 ml.) and the washings were evaporated in vacuo, Toluene was added and the residue was evaporated in vacuo. 3,3-Di-(hydroxymethyl)-hexan-1-ol was obtained as a colourless oil and was used without further purification.

Workup

  1. temperaturerefluxed
  2. stirringwith stirring for four hours
  3. customThe solid was removed by filtration
  4. washwashed with water (40 ml.) The combined filtrates and washings
  5. customwere evaporated in vacuo
  6. washThe residue was washed with acetone (3×100 ml)
  7. customThe acetone washings were evaporated in vacuo
  8. washThe residue was washed with chloroform (3×100 ml.)
  9. customthe washings were evaporated in vacuo, Toluene
  10. additionwas added
  11. customthe residue was evaporated in vacuo

Sources & evidence

ORD record
ord-45034e951f444a7ca2b9ba47e95e7606
Source dataset
uspto-grants-1991_01
Patent number
US04985582

Reaction notes

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