3,3-Dimethylbutanoyl chloride → Methyl [3-(2,2-dimethylpropionamido)-4-hydroxyphenyl]acetate

Participants

Reaction Steps

Sodium hydrogen carbonate (19 g, 0.23 mol) was suspended in 1,2-dimethoxyethane (180 ml), and methyl(3-amino-4-hydroxyphenyl)acetate [from step 4] (26.3 g, 0.145 mole) was added. To this mixture was added, dropwise, a solution of tert-butylacetyl chloride in 1,2-dimethoxyethane (45 ml), over 2 hours. Once the addition was complete, the mixture was stirred at room temperature for 1 hour. The mixture was filtered, the inorganic solid washed with ethyl acetate (3×50 ml) and the filtrate and washings were combined and concentrated. Trituration of the product with hexane gave methyl [3-(2,2-dimethylpropionamido)-4-hydroxyphenyl]acetate (40.1 g) as an off-white solid, m.p. 112-113° C.

Provenance & Evidence