Water → Oct-2-en-4-ol

HRID 985929Notes

Reaction equation

HRID 985929 reaction equation
[CH:1](=[O:5])/[CH:2]=[CH:3]/[CH3:4].[CH2:6]([Li])[CH2:7][CH2:8][CH3:9].O>C1(C)C=CC=CC=1>[CH3:4][CH:3]=[CH:2][CH:1]([OH:5])[CH2:6][CH2:7][CH2:8][CH3:9]

Participants

5

Reactant 3

HCID 962WaterHCID 447466CrotonaldehydeHCID 178418339Butyllithium

Product 1

HCID 89274Oct-2-en-4-olYield 79.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

31.5 g of crotonaldehyde are added dropwise, at -20° C. in the course of 75 minutes, to 32 g of butyllithium, dissolved in 145.8 g of toluene. After the reaction has proceeded for two hours, the temperature increasing slowly to 0° C., 250 ml of water are carefully added dropwise. The aqueous phase is separated off and washed once with 100 ml of toluene. The combined organic phases are washed neutral with water, dried over sodium sulphate and distilled. 46 g of oct-2-en-4-ol of boiling point 68°-72° C./13 mb are obtained. According to the gas chromatogram, the purity is 96%. The NMR spectrum confirms the expected structure.

Workup

  1. customThe aqueous phase is separated off
  2. washwashed once with 100 ml of toluene
  3. washThe combined organic phases are washed neutral with water
  4. dry with materialdried over sodium sulphate
  5. distillationdistilled

Sources & evidence

ORD record
ord-bab572eaf3c6438cbe77c7540fb09270
Source dataset
uspto-grants-1987_12
Patent number
US04710392

Reaction notes

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