ChemicalBook CAS DataBase List Benzoic acid,2-methyl-, 1,1-dimethylethyl ester

Benzoic acid,2-methyl-, 1,1-dimethylethyl ester synthesis

14synthesis methods

Product Name:Benzoic acid,2-methyl-, 1,1-dimethylethyl ester
CAS Number:16537-18-1
Molecular formula:C12H16O2
Molecular Weight:192.25

118-90-1 Synthesis

118-90-1
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83766-88-5
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Benzoic acid,2-methyl-, 1,1-dimethylethyl ester

16537-18-1
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Yield: 98%

Reaction Conditions:

with boron trifluoride diethyl etherate in toluene at 20; for 0.5 h;

Steps:

3 General procedure for the preparation of tert-butyl ester compounds (5a-5v)
Carboxylic acid (0.2 g, 1.64 mmol), tert-butoxypyridine (0.33 g, 2.21 mmol) and boron trifluoride diethyl etherate (0.31 g, 2.21 mmol) in dry PhCH3 (2 mL) were added to a 20-ml vial. The reaction mixture was then allowed to stir at room temperature for 30 min before quenching with anhydrous NaHCO3. The reaction mixture was diluted with ethyl acetate (30 mL), then washed with water (20 mL), followed by brine (20 mL). The organic layer was dried over anhydrous sodium sulfate and carefully concentrated under reduced pressure. The resulting residue was then purified by flash column chromatography on silica gel with 0:4 to 1:4 dichloromethane/hexane as eluent to yield the desired product 5a as a colorless oil.

References:

La, Minh Thanh;Kim, Hee-Kwon [Tetrahedron,2018,vol. 74,# 27,p. 3748 - 3754]

933-88-0 Synthesis