Hydrochloric Acid → HCID 88313714, compound

Participants

Reaction Steps

A solution of ethyl (2E,4E)-7-phenylhepta-2,4-dienoate (7.32 g) in dry toluene (75 ml) was cooled to −78° C. DIBAL-H (1M in hexanes, 65.2 ml) was added dropwise and the mixture was stirred for 3 h. The mixture was allowed to warm-up to room temperature and hydrolyzed with 1M aqueous HCl with cooling in ice/water bath. Additional, 3M aqueous HCl was added until pH=1. The layers were separated and the aqueous layer was extracted three times with EtOAc. The combined organic layer was washed with brine, dried over Na2SO4 and concentrated. The crude product was purified by column chromatography to yield a colorless oil.

Provenance & Evidence