Trichloroisocyanuric Acid → Methyl 2,2-dimethyl-3-oxopropanoate

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Reaction Conditions

Reaction Steps

Methyl 3-hydroxy-2,2-dimethyl-propanoate (52.4 g, 396.49 mmol) is dissolved in dichloromethane (495 mL) and the mixture is cooled in an ice-water bath. Trichloroisocyanuric acid (101.36 g, 436.14 mmol) is added portionwise, followed by 2,2,6,6-tetramethylpiperidine-N-oxide (6.20 g, 39.65 mmol). The mixture is stirred at 0° C. for 15 min and then allowed to warm to RT and stirred for an additional 60 min. The solid is then filtered through CELITE® and rinsed with dichloromethane (300 mL). The filtrate is washed with a saturated solution of Na2CO3 in water. The organic phase is dried over Na2SO4, filtered, and concentrated under reduced pressure to afford the title compound (41.24 g, 80%) as a greenish oil. The product is used without further purification in the next reaction step. 1H NMR (400 MHz, CDCl3); δ 1.34 (6H, s), 1.34 (6H, s), 3.74 (3H, s), 9.64 (1H, s).

Provenance & Evidence