ChemicalBook CAS DataBase List 4-TERT-BUTYL-2-ETHOXY-BENZOIC ACID

4-TERT-BUTYL-2-ETHOXY-BENZOIC ACID synthesis

4synthesis methods

Product Name:4-TERT-BUTYL-2-ETHOXY-BENZOIC ACID
CAS Number:73469-54-2
Molecular formula:C12H16O3
Molecular Weight:208.25

Benzoic acid, 5-(1,1-dimethylethyl)-2-methoxy-, methyl ester

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Yield: 96%

Reaction Conditions:

with sodium hydroxide in methanol;water at 20; for 3 h;

Steps:

3.c
5-(tert-Butyl)-2-methoxybenzoyl chloride (6a, Scheme 2). To a solution of 3.8 g of 5-(tert-butyl)-2-methoxybenzoic acid methyl ester in MeOH (30 mL) was added 50% NaOH-water solution (1 mL). The resulting solution was stirred at room temperature for 3 hr. After the reaction was complete, the pH was adjusted to pH=2-3 using 1M HCl. The reaction mixture was collected by extraction with ethylacetate and water three times. The organic layer was dried over anhydrous magnesium sulfate (MgSO4) and evaporated under reduced pressure. After recrystallization, the final product yielded 3.4 g (96%). Without further purification a solution of 3.4 g of 5-(tert-butyl)-2-methoxybenzoic acid in 20 mL CH2Cl2 was slowly treated with SOCl2 (1.2 eq). The resulting solution was stirred at room temperature for 2 hr. The reaction mixture was evaporated under reduced pressure and dried in a vacuum oven overnight to yield 3.4 g (91.9%).

References:

Welsh, William J.;Yu, Seong Jae;Nair, Anil US2003/225072, 2003, A1 Location in patent:Page 7; 13