Water → 2-Propylbutane-1,4-diol

HRID 1788639Notes

Reaction equation

HRID 1788639 reaction equation
[CH2:1]([CH:4]([CH2:10][C:11](OCC)=[O:12])[C:5](OCC)=[O:6])[CH2:2][CH3:3].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[Al]>C(OCC)C>[OH:6][CH2:5][CH:4]([CH2:1][CH2:2][CH3:3])[CH2:10][CH2:11][OH:12]

Participants

6

Reactant 4

HCID 962WaterHCID 5359268AluminumHCID 21226445Aluminium lithium hydrideHCID 21856079HCID 21856079, compound

Product 1

HCID 125082552-Propylbutane-1,4-diolYield 67%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of diethyl 2-prop-1-ylsuccinate (23.47 g) in diethyl ether (100 ml) was added dropwise to a cooled and stirred suspension of lithium aluminium hydride (6.19 g) in dry diethyl ether (500 ml) under an atmosphere of nitrogen. When the addition was complete, the reaction mixture was stirred at room temperature for 1.5 hours, then enough water to hydrolyse both the excess reducing agent and the intermediate aluminium complexes was added. The resulting solids were filtered off and the filtrate was dried over magnesium sulphate and concentrated to give 3-hydroxymethylhexan-1-ol (9.58 g, 67%) as a colourless oil.

Workup

  1. temperaturea cooled
  2. additionWhen the addition
  3. stirringthe reaction mixture was stirred at room temperature for 1.5 hours
  4. filtrationThe resulting solids were filtered off
  5. dry with materialthe filtrate was dried over magnesium sulphate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-c66b4c32006947549b21495daa76d09c
Source dataset
uspto-grants-1987_08
Patent number
US04684396

Reaction notes

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