Toluene → Ethyl 2,2-dimethoxyethylcarbamate

Participants

Reaction Conditions

Reaction Steps

A two-liter, three-necked round bottom flask was fitted with a 125-mL addition funnel and a digital thermometer probe. To this flask was added 65 g (618 mmol) of aminoacetaldehyde dimethyl acetal, 310 mL of toluene, and a solution of 27.8 g (695 mmol) of NaOH in 155 mL of water. This reaction mixture was cooled to 10° C. via ice bath. Ethyl chloroformate (59.1 mL, 618 mmol) was then added dropwise to the reaction mixture via addition funnel over a 15-20 minute period making sure the reaction temperature stayed near 10° C. Once addition was complete the reaction was stirred at room temperature for two hours. The aqueous layer was then separated, saturated with solid sodium chloride, and extracted with 3×50 mL of toluene. The toluene layers were combined, dried over magnesium sulfate, filtered, and concentrated in vacuo.

Provenance & Evidence