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Benzoic acid,2,4-diMethoxy-6-Methyl-,2- Methylpropyl ester synthesis
- Product Name:Benzoic acid,2,4-diMethoxy-6-Methyl-,2- Methylpropyl ester
- CAS Number:1276019-92-1
- Molecular formula:C14H20O4
- Molecular Weight:252.31
Yield:1276019-92-1 89%
Reaction Conditions:
Stage #1: 2-bromo-1,5-dimethoxy-3-methylbenzenewith n-butyllithium in tetrahydrofuran at -78; for 1 h;
Stage #2: isobutyl chloroformate in tetrahydrofuran at -78 - 20; for 2 h;
Steps:
Preparation of compound 7
To a solution of 8 (5.00 g, 21.64 mmol) in THF (40 mL) at -78 °C was added n-BuLi (2.2 M, 11.79 mL, 25.94 mmol) dropwise. After the mixture was stirred at -78 °C for 1 h, isobutyl chloroformate (3.84 g, 28.12 mmol) was added slowly. The reaction mixture was allowed to reach room temperature in 2 h, and the reaction was quenched with a saturated solution of NH4Cl. THF was removed in vacuo. The reaction mixture was extracted with ethyl acetate (3x30 mL). The organic layers were combined, washed with brine (3x30 mL), dried over anhydrous MgSO4 and concentrated. The residue was subjected to silica gel chromatographic with petroleum ether/EtOAc (25:1) to give 7 (4.86 g, 89%) as a colorless oil.
References:
Jiang, Cheng-Shi;Zhou, Rong;Gong, Jing-Xu;Chen, Li-Li;Kurtán, Tibor;Shen, Xu;Guo, Yue-Wei [Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,# 4,p. 1171 - 1175] Location in patent:supporting information; experimental part