Ethyl orthoformate → 2-Pentadecynal diethylacetal

Participants

Reaction Steps

1-Tetradecyne (100 g), (EtO)3CH (200 ml) and ZnI2 (15 g) were heated together (bath temperature 170°-175°) with distillative removal of ethanol (~90 minutes). The reaction mixture was evaporated in vacuo (bath temperature 80°) to remove excess (EtO)3CH. The residue was distributed between CH2Cl2 and water. The CH2Cl2 phase was separated, washed with aqueous NaHCO3, dried (Na2SO4) and evaporated in vacuo to provide a light brown oil. Yield: 135.4 g. This product was shown to be virtually pure by TLC and PMR and it was used as such in subsequent reactions.

Provenance & Evidence