| Identification | More | [Name]
METHYL 3-HYDROXY-2-NAPHTHOATE | [CAS]
883-99-8 | [Synonyms]
2-HYDROXY-3-NAPHTHOIC ACID METHYL ESTER
3-HYDROXY-2-NAPHTHOIC ACID METHYL ESTER
METHYL 2-HYDROXY-3-NAPHTHOATE
METHYL 3-HYDROXY-2-NAPHTHOATE
METHYL BETA-HYDROXYNAPHTHOATE
METHYL B-HYDROXYNAPHTHOATE
2-Naphthalenecarboxylic acid, 3-hydroxy-, methyl ester
3-hydroxy-2-naphthalenecarboxylicacimethylester
beta-Hydroxynaphthoic acid methyl ester
Methyl 3-hydroxy-2-naphthalenecarboxylate
3-Hydroxynaphthalene-2-carboxylic acid methyl ester (BON Me)
Methyl-3-hydroxy-2-naphthoat
Methyl 3-hydroxy-2-naphthoate, 98+%
3-(Methoxycarbonyl)-2-naphthol
3-Hydroxy-2-naphthalenecarboxylic acid methyl ester | [EINECS(EC#)]
212-936-9 | [Molecular Formula]
C12H10O3 | [MDL Number]
MFCD00004099 | [Molecular Weight]
202.21 | [MOL File]
883-99-8.mol |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [WGK Germany ]
2
| [F ]
9-23 | [TSCA ]
Yes | [HS Code ]
2918.29.7500 |
| Hazard Information | Back Directory | [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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