Diisopropylamine → 2-(Carboxymethyl)-4-methoxybenzoic acid

Temperature

0 °C

A solution of diisopropylamine (3.43 ml, 24.07 mmol) in THF (3 mL) was cooled to −78° C. and n-butyllithium (9.63 ml, 24.07 mmol) was added dropwise and allowed the solution to warm to 0° C. for 5 min and then re-cooled to −78° C. 4-methoxy-2-methylbenzoic acid (1 g, 6.02 mmol) and dimethyl carbonate (1.013 ml, 12.04 mmol) in THF (3 mL) was added dropwise. After the addition is complete, the reaction is allowed to slowly warm to RT and stir for 4 h. The reaction was quenched with 10 mL of H2O and allowed to stir for 16 h. The layers were separated, washed the organics with H2O (2×), combined all the aqueous extractions and adjusted the pH to 2-3 with 6N HCl while in an ice bath. The resulting in a white precipitate was filtered and dried under vacuum to afford the title compound (1.09 g, 86%) as a white solid. LCMS (ES+) m/z 211.05 (M+H)+.

1. temperaturere-cooled to −78° C
2. additionAfter the addition
3. temperatureto slowly warm to RT
4. customThe reaction was quenched with 10 mL of H2O
5. stirringto stir for 16 h
6. customThe layers were separated
7. washwashed the organics with H2O (2×)
8. extractionthe aqueous extractions
9. filtrationThe resulting in a white precipitate was filtered
10. customdried under vacuum

ORD record

ord-66aed390e84d4956bf1a516d39352e14

Source dataset

uspto-grants-2013_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08461107B2