| Identification | Back Directory | [Name]
Methyl 3-hydroxy-4-methoxybenzoate | [CAS]
6702-50-7 | [Synonyms]
METHYL ISOVANILLATE
RARECHEM AL BF 0068
Methyl 3-hydroxy-4-m
METHYL 3-HYDROXY-4-METHOXYBENZOATE
Methyl 3-hydroxy-4-methoxybenzoate,98%
Methyl 3-hydroxy-4-methoxybenzoate 98%
METHYL 3-HYDROXY-4-METHOXYBENZENECARBOXYLATE
3-Hydroxy-4-Methoxy-benzoic acid Methyl ester
3 - hydroxy - 4 - Methoxy Methyl benzoic acid
benzoic acid, 3-hydroxy-4-methoxy-, methyl ester
Methyl 3-hydroxy-4-methoxybenzoateMethyl isovanillate
2-Methoxy-5-(methoxycarbonyl)phenol, 2-Hydroxy-4-(methoxycarbonyl)anisole, Methyl isovanillate | [Molecular Formula]
C9H10O4 | [MDL Number]
MFCD01321262 | [MOL File]
6702-50-7.mol | [Molecular Weight]
182.17 |
| Chemical Properties | Back Directory | [Appearance]
Off-white to beige crystalline powder | [Melting point ]
64-67 °C(lit.)
| [Boiling point ]
102 °C(Press: 0.1 Torr) | [density ]
1.216±0.06 g/cm3(Predicted) | [storage temp. ]
Sealed in dry,Room Temperature | [form ]
powder to crystal | [pka]
9.15±0.10(Predicted) | [color ]
Light yellow to Brown | [InChI]
InChI=1S/C9H10O4/c1-12-8-4-3-6(5-7(8)10)9(11)13-2/h3-5,10H,1-2H3 | [InChIKey]
QXOXUEFXRSIYSW-UHFFFAOYSA-N | [SMILES]
C(OC)(=O)C1=CC=C(OC)C(O)=C1 | [LogP]
1.750 (est) |
| Hazard Information | Back Directory | [Chemical Properties]
Off-white to beige crystalline powder | [Uses]
Methyl 3-hydroxy-4-methoxybenzoate may be used as starting reagent in the novel synthesis of gefitinib. Synthesis involves the alkylation of starting material, followed by nitration, reduction, cyclization, chlorination and two successive amination reactions. It may be used as starting reagent in the synthesis of methyl 5-(benzo[d][1,3]dioxol-5-yl)-4-methoxy-2-nitrobenzoate. | [Synthesis]
To a dry 100 mL three-necked flask, 10 g of 3-hydroxy-4-methoxybenzoic acid, 110 mL of methanol, and 360 μL of concentrated sulfuric acid were sequentially added, and the mixture was heated to 65 °C and reacted under magnetic stirring overnight. The reaction process was monitored by thin layer chromatography (unfolding agent: ethyl acetate/dichloromethane=1:1). Upon completion of the reaction, the reaction mixture was transferred to a round bottom flask and methanol was removed by distillation under reduced pressure. The residue was extracted with 25 mL of ethyl acetate and neutralized with 15 mL of saturated sodium bicarbonate solution. After evaporation of ethyl acetate, the solid product methyl 3-hydroxy-4-methoxybenzoate was obtained as 9.06 g in 83.6% yield. | [References]
[1] Patent: WO2005/9389, 2005, A2. Location in patent: Page/Page column 139
[2] Patent: WO2005/9389, 2005, A2. Location in patent: Page/Page column 139
[3] Journal of Organic Chemistry, 1985, vol. 50, # 2, p. 217 - 231
[4] Bioorganic and Medicinal Chemistry Letters, 2002, vol. 12, # 20, p. 2893 - 2897
[5] Organic and Biomolecular Chemistry, 2016, vol. 14, # 11, p. 3061 - 3068 |
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