Toluene → HCID 131732701, compound

Participants

Reaction Conditions

Reaction Steps

The following reagents were charged in a stainless steel autoclave: above-obtained alcohol (9.5 g; 62.4 mmol); triethyl orthoacetate (23.14 g; 140 mmol); 2-ethylhexanoic acid (0.24 g; 1.7 mmol) and toluene (18 ml). The autoclave was purged with nitrogen and heated in an oil bath at 200° C. overnight. After cooling to room temperature, the reaction was poured onto water. A few drops of 5% aq. HCl were added. The mixture was extracted twice with diethyl ether. Each organic phase was washed with water, aqueous saturated NaHCO3 and brine (3×). Combined extracts were dried over sodium sulfate. The product was purified by column chromatography on silica gel (eluent: heptanes/ethyl acetate 9:1) followed by bulb-to-bulb distillation (120° C./0.01 mbar). The product was obtained (yield: 79%) as a 98:2 mixture of E and Z isomers.

Provenance & Evidence