Reaction #324421

Reaction equation

6-methoxy-1-naphthoic acid

thionyl chloride

→

6-methoxy-1-naphthoyl chloride

Conditions

Workup

1. 1
   Temperaturethe solution was heated
2. 2
   Temperatureto reflux for 3 hours
3. 3
   Concentrationthe mixture was concentrated under reduced pressure

Procedure

Under an argon atmosphere, 6-methoxy-1-naphthoic acid (synthesized by the process of J. D. Moseley and J. P. Gilday, Tetrahedron, 62, 4690-4697 (2006)) (1.20 g, 5.93 mmol) was dissolved in thionyl chloride (5.00 mL, 68.8 mmol) and the solution was heated to reflux for 3 hours. After cooling to room temperature, the mixture was concentrated under reduced pressure to give the crude product of 6-methoxy-1-naphthoyl chloride (22) as a colorless oil. The product was used in the following reaction without further purification.

Source