3-Methoxybenzaldehyde → Methyl 5-(3-methoxyphenyl)penta-2,4-dienoate

Participants

Reaction Conditions

Reaction Steps

A mixture of potassium tert-butoxide (52 g) and tert-butanol (170 ml) was treated dropwise with a mixture of 3-methoxybenzaldehyde (30 g) and methyl crotonate (35 ml). The temperature of the reaction mixture rose to 80° C. during the addition and was then maintained for a further 3 hours at 65° C. The reaction mixture was cooled to room temperature, poured into ice/water and washed with diethyl ether. The aqueous phase was acidified with concentrated HCl and extracted with ethyl acetate. The organic phase was washed with brine, dried (MgSO4) and evaporated under reduced pressure to yield an orange oil. Yield 53.2 g. Used directly in the next step.

Provenance & Evidence