1-Propanol → Propyl 2-hydroxy-3-naphthoate

Temperature

120 °C

3-Hydroxy-naphthalene-2-carboxylic acid (2 g) was dissolved in 1-propanol (10 ml) to prepare a solution which was then brought to 0° C. Thionyl chloride (1.16 ml) was gradually added dropwise to the solution, and the mixture was stirred at 120° C. for 2 hr. The reaction solution was cooled to room temperature, and the solvent was removed by distillation under the reduced pressure. Water was then added to the residue, and the mixture was extracted with chloroform. The chloroform layer was washed with saturated brine and was dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by column chromatography using chloroform to give propyl 3-hydroxy-naphthalene-2-carboxylate (2.15 g, yield 88%).

1. customto prepare a solution which
2. customwas then brought to 0° C
3. temperatureThe reaction solution was cooled to room temperature
4. customthe solvent was removed by distillation under the reduced pressure
5. additionWater was then added to the residue
6. extractionthe mixture was extracted with chloroform
7. washThe chloroform layer was washed with saturated brine
8. dry with materialwas dried over anhydrous sodium sulfate
9. customThe solvent was removed by distillation under the reduced pressure
10. customthe residue was purified by column chromatography

ORD record

ord-ea72b2300ed74a91a42f445664fea137

Source dataset

uspto-grants-2009_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07560558B2