Diethylcarbamoyl chloride → 1-Naphthyl carbamate

Participants

Reaction Steps

Sibi et al (J. Org. Chem., 48 (11), 1935-1937, 1983) disclose reaction of 1-naphthol with diethyl carbamyl chloride in pyridine to produce a 1-naphthyl carbamate. Treatment of 1-naphthyl carbamate under the standard conditions for methylation of tertiary amides (1.1 equiv. sec-BuLi/TMEDA/THF/-78° C./1 hour) followed by quenching with methyl iodide, warming to room temperature (8 to 12 hours) and NH4Cl work-up, afforded 2-methyl-1-naphthyl carbamate in a yield of 90%. Carbamate removal was effected in a yield of 90% by reduction (LAH/THF/reflux;H+) or hydrolysis (NaOH/aqueous CH3OH or HO(CH2)2OH/reflux) to yield 2-methyl-1-naphthol.

Provenance & Evidence