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846055-82-1

2-(2-Methoxyvinyl)-6-nitrobenzoic Acid Methyl Ester synthesis

4synthesis methods
2-FORMYL-6-NITROBENZOIC ACID METHYL ESTER

142314-70-3
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4009-98-7 Synthesis
(Methoxymethyl)triphenylphosphonium chloride

4009-98-7
365 suppliers
$5.00/10g

2-(2-Methoxyvinyl)-6-nitrobenzoic Acid Methyl Ester

846055-82-1
7 suppliers
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Yield:846055-82-1 66%

Reaction Conditions:

Stage #1: (methoxymethyl)triphenylphosphonium chloridewith sodium hydride in tetrahydrofuran at 20;Inert atmosphere;
Stage #2: methyl 2-formyl-6-nitrobenzoate in tetrahydrofuran at 20;

Steps:

16.16-4 [16-4] Synthesis of Compound

To the stirred suspension of (methoxymethyl)triphenyl phosphonium chloride (1.22 g, 3.59 mmol) dissolved in THF (24 ml), sodium hydride (192 mg, 4.78 mmol) was added in small portions in an ice container under N2. The red solution was stirred at a room temperature for 30 minutes, and then compound (500 mg, 2.39 mmol) dissolved in THF (6 ml) was added dropwise. The reactants were stirred at a room temperature for 12 hours. The mixture was diluted with water, and was extracted with EtOAc (50 ml). The combined organic layer was washed with salt water, and was dried on MgSO4, and the solvent was removed under vacuum to obtain dark oil. The crude compound was purified by silica-gel column chromatography using EtOAc/Hex (30%) as an eluent, to obtain compound (372 mg, 1.57 mmol, 66%) as yellow oil (mixture of 1.7:1 E/Z isomers).

References:

US2020/62730,2020,A1 Location in patent:Paragraph 0210-0211