Diethyl Ether → Benzylacetylene

HRID 1534752Notes

Reaction equation

HRID 1534752 reaction equation
C([Li])CCC.CCOCC.[C:11]1([C:17]#[C:18][CH3:19])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>O>[CH2:17]([C:18]#[CH:19])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 69601MethylphenylacetyleneHCID 178418339Butyllithium

Product 1

HCID 575753Benzylacetylene

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
5 °C

Procedure

A solution of n-butyl lithium (2.5 M in hexane; 35 ml, 43.1 mmol) was added to dry ether (100 ml) under argon. The stirred solution was cooled to 5° C. and 1-phenyl-1-propyne (5.0 g, 43.1 mmol) was slowly added. On warming to room temperature the mixture turned bright red. After 18 hours, the mixture was cooled to 0° C., water was added, and the ether layer was separated. Concentration under reduced pressure gave an oil which was distilled to give benzyl acetylene as an oil.

Workup

  1. temperatureOn warming to room temperature the mixture
  2. temperaturethe mixture was cooled to 0° C.
  3. customthe ether layer was separated
  4. concentrationConcentration under reduced pressure
  5. customgave an oil which
  6. distillationwas distilled

Sources & evidence

ORD record
ord-ade746c587de44a4a5342f4012adf4d3
Source dataset
uspto-grants-1992_02
Patent number
US05090992

Reaction notes

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