Ethyl formate → 3-(m-Tolyl)propiolaldehyde

HRID 2254447Notes

Reaction equation

HRID 2254447 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH3:9])[CH:6]=[CH:7][CH:8]=1)#[CH:2].[CH:10](OCC)=[O:11]>C(OCC)C>[CH3:9][C:5]1[CH:4]=[C:3]([C:1]#[C:2][CH:10]=[O:11])[CH:8]=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 8025Ethyl formateHCID 1366003-Methylphenylacetylene

Product 1

HCID 107731013-(m-Tolyl)propiolaldehydeYield 47%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
-70 °C

Procedure

1.56 g of 3-ethynyltoluene was dissolved in 20 ml of ethyl ether, and with stirring at -70° C., 8.5 ml of 1.5M n-butyllithium-hexane solution and 1.2 ml of ethyl formate were added. The mixture was stirred at the same temperature for 20 minutes. The reaction mixture was poured into ice water, and the organic layer was separated. The solvent was evaporated to give 900 mg (yield 47%) of 3-(3-methylphenyl)-2-propynaldehyde as a colorless oil.

Workup

  1. stirringThe mixture was stirred at the same temperature for 20 minutes
  2. customthe organic layer was separated
  3. customThe solvent was evaporated

Sources & evidence

ORD record
ord-3f5b874af5ab4918a99aac8d3d1a64d9
Source dataset
uspto-grants-1993_08
Patent number
US05234946

Reaction notes

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