4-Hydroxybenzaldehyde → Tert-butyl 2-(4-formylphenoxy)acetate

Participants

Reaction Conditions

Reaction Steps

366 g of dimethylformamide and 165.9 g (1.2 mol) of potassium carbonate were placed in a flask, followed by dropwise addition of 122 g (1 mol) of 4-hydroxybenzaldehyde. 181.2 g (1.2 mol) of t-butyl chloroacetate were added dropwise to the mixture at a temperature of 50° C. for two hours. After the addition, the mixture was stirred for two hours at a temperature of 50° C. and then another seven hours at a temperature of 70° C. The resulting reaction mixture was washed with 122 g of toluene and 662 g of water. 100 g of the solvent was removed from the mixture by distillation under reduced pressure and then 236 g of n-heptane were added to the distillation residue to effect crystallization. The resulting crystals were collected by filtration to provide 128.4 g of 4-t-butoxycarbonylmethoxybenzaldehyde having a purity of 99.9% as white crystals. FIG. 2 is an infrared absorption spectrum of the compound. The yield was 54%.

Provenance & Evidence