Potassium Iodide → Veratrole

Participants

Reaction Steps

A solution containing 147.0 g (306 mmol) of the tetraethyl stilbene-4,4'-bis(methylenephosphonate) described in (c) above and 129.4 g (673 mmol) of the 4-allyloxy-3-methoxybenzaldehyde described in Example 2 (b) above in 900 ml of anisole, is added dropwise with stirring and at a temperature of 0° to 10° C. to a suspension containing 94.4 g (841 mmol) of potassium tert-butylate, 6.1 g (23 mmol) of 18-crown-6 and 1.75 g (10 mmol) of potassium iodide in 1300 ml of anisole. The mixture is then stirred at room temperature for an additional 1 hour and then at 110° C. for an additional 3 hours. The mixture is cooled to room temperature and the resultant solid is filtered off with suction and recrystallized first from dimethyl sulfoxide and then from veratrol (1,2-dimethoxybenzene), giving 119.5 g of yellow crystals, which corresponds to a yield of 73%.

Provenance & Evidence