Tetrahydrofuran → HCID 24795835, compound

Participants

Reaction Steps

In a nitrogen atmosphere, a mixture of 48.1 g of 2-isopropyl-5-methyl-2,4-hexadienoic acid (2) having a purity of 98.0% and an (E)-isomer purity of 98.1% and 300 ml of tetrahydrofuran was added dropwise to a mixture of 20.0 g of lithium aluminum hydride and 500 ml of tetrahydrofuran over 70 minutes, which was stirred under ice cooling. The reaction mixture was stirred under ice cooling for 30 minutes and then stirred at room temperature for 17.5 hours, and subjected to careful and sequential additions of 50 g of ethyl acetate, 20.7 g of water, 12.42 g of 25% aqueous sodium hydroxide solution, and 70.38 g of water. The crystals thus formed were filtered. The filtrate was dried and concentrated to obtain 54.99 g of crude intended product having a purity of 76.8% and containing 16.4% of the solvent. The yield was 98%.

Provenance & Evidence