Methyl 4-(benzyloxy)-5-methoxy-2-nitrobenzoate synthesis
- Product Name:Methyl 4-(benzyloxy)-5-methoxy-2-nitrobenzoate
- CAS Number:61032-41-5
- Molecular formula:C16H15NO6
- Molecular Weight:317.29
56441-97-5
61032-41-5
4.1.4 Synthesis of methyl 4-benzyloxy-5-methoxy-2-nitrobenzoate (12): intermediate 11 (10.1 g, 37 mmol) was suspended in acetic acid (100 mL) and 70% nitric acid (20 mL) was added slowly. Subsequently, the reaction mixture was heated to 50 °C and maintained at this temperature for 5 hours. Upon completion of the reaction, the mixture was cooled to room temperature and poured into ice water (500 mL). After stirring for 1 hour, the precipitate precipitated was collected by filtration, washed with water and dried to give nitro compound 12 as a white solid. Yield: 86%, melting point: 126-128°C.
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Yield: 80%
Reaction Conditions:
with thionyl chloride at 60; for 96 h;Inert atmosphere;
Steps:
6 4-Benzyloxy-3-methoxy-2-nitrobenzoic acid methyl ester (24)
Under argon, at room temperature, to a suspension of (19) (4.0 g, 131 mmol) in absolute methanol (100 mL) was added dropwise thionyl chloride (1.9 mL, 262 mmol). The resulting mixture was stirred at 60°C for 96 hrs then concentrated under reduced pressure until few volume. The residue was allowed to crystallize at -20°C and the solid was collected by filtration affording 4-benzyloxy- (0294) 3-methoxy-2-nitrobenzoic acid methyl ester (24) (3.36 g, 80%) as a white crystal. LCMS CieHisNOe Rt = 6.862 min, ESI+ m/z = 318.9 (M+H), 285.9 (M-OMe).
References:
INSERM (INSTITUT NATIONAL DE LA SANTÉ ET DE LA RECHERCHE MÉDICALE);INSTITUT JEAN PAOLI & IRENE CALMETTES;AIX-MARSEILLE UNIVERSITÉ;CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE (CNRS) WO2021/74392, 2021, A1 Location in patent:Page/Page column 44-45
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61032-41-5
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61032-41-5
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