Propanal → HCID 86757532, compound

Participants

Reaction Conditions

Reaction Steps

Into a 2 L Morton flask equipped with a mechanical air stirrer, temperature probe, Nitrogen inlet, autojack, and cooling bath was placed methanol (350 mL) and NaOH (31.25 g, 0.78 mol) dissolved in water (93.75 mL). 2-Methyl-3-phenyl-propanal (100 g, 0.68 mol) was added to the resulting mixture with stirring at 20° C. Over a period of 5 hours at an exponentially decreasing rate, propionaldehyde (48.82 mL, 39.25 g, 0.68 mol) was added to the mixture via a syringe pump while maintaining the reaction temperature at 14-20° C. The following propionaldehyde addition rate profile was used: 0.179 mL/min for two hours; 0.162 mL/min for one hour; and 0.147 mL/min for two hours. The reaction mixture was stirred for an additional 20 min at 14-20 ° C. Acetic acid (47 mL) was then added to the reaction mass followed by 100 mL of a saturated aqueous solution of sodium chloride. The mixture was extracted with two 100 mL portions of MTBE. The organic layers were combined and washed with two 100 mL portions of a saturated aqueous solution of sodium bicarbonate solution then with a saturated aqueous solution of.sodium chloride, dried (MgSO4), filtered, and roto-evaporated to give 2, 4-dimethyl-5-phenylpent-2-enal as a yellow liquid isomeric mixture (118.9 g).

Provenance & Evidence