METHYL 3-HYDROXY-2-NAPHTHOATE Chemical Properties

Melting point:

73-75 °C (lit.)

Boiling point:

205-207 °C (lit.)

Density 

1.1868 (rough estimate)

refractive index 

1.5440 (estimate)

Flash point:

205-207°C/160mm

storage temp. 

Inert atmosphere,Room Temperature

form 

powder to crystal

pka

9.36±0.40(Predicted)

color 

Light yellow to Yellow to Orange

BRN 

1074526

CAS DataBase Reference

883-99-8(CAS DataBase Reference)

EPA Substance Registry System

2-Naphthalenecarboxylic acid, 3-hydroxy-, methyl ester (883-99-8)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

2

F 

9-23

TSCA 

Yes

HS Code 

2918.29.7500

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

METHYL 3-HYDROXY-2-NAPHTHOATE Usage And Synthesis

General Description

Methyl 3-hydroxy-2-naphthoate undergoes asymmetric oxidative coupling using mono-N-alkylated octahydrobinaphthyl-2,2′-diamine chiral ligands.

Synthesis

Methyl 3-hydroxy-2-naphthoate is obtained by reacting 3-hydroxy-2-naphthoic acid with methanol in sulphuric acid.3-hydroxy-2-naphthoic acid (1.00 g, 5.31 mmol) was dissolved in methanol (20 ml) and concentrated sulphuric acid (1 ml) and left to reflux overnight with stirring. The reaction mixture was washed with brine (2×10 ml) and extracted with ethyl acetate (3 × 10 ml) upon cooling. The organic extracts were collected, dried with magnesium sulphate and concentrated in vacuo to give the title compound as a yellow powder (976 mg, 91%): mp: 81℃(Lit.: 75 – 76℃);
vmax/cm-1 3178 br. m (O-H), 2952 w (aro. C-H), 1515 m (aro. C=C); δH (300 MHz; CDCl3) 10.47 (1H, s, OH), 8.47 (1H, s, C(1)H), 7.79 (1H, d, J 8.3, C(5)H or C(8)H), 7.68 (1H, d, J 8.3, C(5)H or C(8)H), 7.50 (1H, td, J 7.5, 1.1, C(6)H or C(7)H), 7.36-7.29 (2H, m, C(4)H and C(6)H or C(7)H), 4.02 (3H, s, OCH3); δC (75 MHz; CDCl3) 170.3 (Ar- C), 156.3 (Ar-C), 137.9 (Ar-C), 132.5 (Ar-CH), 129.2 (Ar-CH), 129.1 (Ar-CH), 127.1 (Ar-C), 126.3 (Ar-CH), 124.0 (Ar-CH), 114.2 (Ar-C), 111.7 (Ar-CH), 52.6 (OCH3); m/z (-ES) 201 (100%, [M-H]-), 202 (14%, [M]-).

Purification Methods

Crystallise the ester from MeOH (charcoal) containing a little water. [Beilstein 10 IV 1186.]

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