ETHYL 6-HYDROXY-2-NAPHTHOATE

ETHYL 6-HYDROXY-2-NAPHTHOATE Property

Melting point:

139-140.5 °C(Solv: ethanol (64-17-5))

Boiling point:

378.7±15.0 °C(Predicted)

Density 

1.225±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

pka

8.83±0.40(Predicted)

Appearance

Light brown to brown Solid

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

ETHYL 6-HYDROXY-2-NAPHTHOATE Chemical Properties,Usage,Production

Synthesis

1. 6-Hydroxy-2-naphthalenecarboxylic acid (5.29 g, 28.0 mmol) was dissolved in ethanol (50 mL) at 0 °C, and thionyl chloride (6 mL) was added slowly. 2. The reaction mixture was stirred at room temperature for 72 h. 3. Upon completion of the reaction, the excess reagent was removed by rotary evaporation. 4. The residue was dissolved in ethyl acetate (100 mL), and washed with water (80 mL), cold 1M sodium bicarbonate solution (80 mL) and brine (80 mL). 5. （The residue was dissolved in ethyl acetate (100 mL) and washed sequentially with water (80 mL), cold 1 M sodium bicarbonate solution (80 mL) and brine (80 mL). 5. The organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated to give ethyl 6-hydroxy-2-naphthoate in 99% yield. 6. The product was characterized by 1H NMR (CDCl3) and LCMS (APCl): 1H NMR (CDCl3): δ 8.53 (1H, br s), 8.5 (1H, br s), 8.3 (1H, br s), 8.4 (1H, br s). , br s), 8.01 (1H, dd, J = 8.5,1.7 Hz), 7.86 (1H, d, J = 8.5 Hz), 7.20-7.13 (2H, m), 4.43 (2H, q, J = 7.3 Hz), 1.43 (3H, t, J = 7.1 Hz). lcmS (apcl): 217.1 (m + h + ).

References

[1] Patent: WO2006/40646, 2006, A1. Location in patent: Page/Page column 97
[2] Journal of Physical Chemistry A, 2016, vol. 120, # 33, p. 6563 - 6574
[3] Journal of Medicinal Chemistry, 2004, vol. 47, # 14, p. 3518 - 3536
[4] Molecular Crystals and Liquid Crystals, 2008, vol. 494, p. 282 - 292
[5] Tetrahedron, 2013, vol. 69, # 43, p. 9045 - 9055