Guaiacol → HCID 18537920, compound

Participants

Reaction Steps

A mixture of 2-methoxyphenol (9.8 mL, 89.3 mmol), dimethylformamide (100 mL) and potassium carbonate (61.5 g, 445 mmol) was stirred at 23° C. while as tert-butyl 2-bromoethylcarbamate (20 g, 89.3 mmol) was added. The mixture was stirred for 24 hours and then poured into ethyl ether:hexanes (1:1, 400 mL) and was washed with water (5×50 mL). The aqueous layer was extracted with ethyl ether:hexanes (1:1, 3×40 mL) and the combined organic layers were dried (Na2SO4) and concentrated in vacuo to provide tert-butyl 2-(2-methoxyphenoxy)ethylcarbamate (23.22 g, 97% yield) as a yellow oil; MS (PB-PCI) C14H21NO4 m/e calc 267.32; found 268 (MH+).

Provenance & Evidence