4-(6-Hydroxyhexoxy)benzaldehyde → (E)-4-Carboxy-4'-[6-hydroxyhexyloxy]-stilbene

Participants

Reaction Steps

0.43 g (62 mmole) of Li was dissolved in 180 ml of ethanol under a nitrogen atmosphere. Then 6.9 g (31 mmole) of 4-(6-hydroxyhexyloxy)-benzaldehyde (15) and 14.8 g (31 mmole) of (4-carboxy-benzyl)-triphenylphosphonium bromide (14) were added. The mixture was stirred for two hours at room temperature. The precipitate was collected on a filter and washed with 50 ml of ethanol. Then the solid was mixed with 1.5 ml of concentrated hydrochloric acid and 35 ml of ethanol. It was stirred for 30 min and the product was collected on a filter. After washing with 50 ml of ethanol and drying in a dessicator 4.1 g of the product were obtained (yield 38%).

Provenance & Evidence