Diethyl Ether → 4-Methoxybenzaldehyde

Participants

Reaction Conditions

Reaction Steps

A mixture of 0.25 mmole PdBr2 [P(C6H5)3 ]2, 19 mmoles tri-n-butylamine and 17.2 mmoles p-bromoanisole was placed in a 45 ml pressure vessel and pressured to 1450 psig with a 1:2 mixture of carbon monoxide and hydrogen. The reaction mixture was heated to 150°C for 10 hrs. with magnetic stirring during which time the gas pressure dropped to 1100 psig. After cooling and venting the reaction mixture was diluted with ether, washed with dilute aqueous hydrochloric acid, dried over anhydrous magnesium sulfate and distilled under reduced pressure. There was obtained 1.97 g of p-methoxybenzaldehyde, b.p. 73°-75°C at 0.7 mm which is 84% of the theoretical amount.

Provenance & Evidence