Dimethylformamide → Methyl 2,6-dimethylbenzoate

Temperature

0 °C

To a cooled (0° C.) solution of 2,6-dimethylbenzoic acid (20.2 g, 134 mmol) in dichloromethane (200 mL) is added DMF (1 mL) followed by oxalyl chloride (14 mL, 162 mmol). On complete addition, the cold bath is removed and stirring continued for 3 h. The resulting solution is concentrated under vacuum and the residue added slowly to a cooled (0° C.) solution comprising methanol (200 mL) and triethylamine (40 mL). On complete addition the reaction mixture is stirred for 30 min. then poured into hydrochloric acid solution (400 mL, 2N) which is then extracted with ether. The ether extract is washed with hydrochloric acid solution (1N), sokium bicarbonate solution and brine; then dried over MgSO4 and concentrated to give the title compound which is used without further purification. MS (EI) 164 (M)+.

1. additionOn complete addition
2. customthe cold bath is removed
3. concentrationThe resulting solution is concentrated under vacuum
4. additionthe residue added slowly to
5. additionOn complete addition the reaction mixture
6. stirringis stirred for 30 min.
7. additionthen poured into hydrochloric acid solution (400 mL, 2N) which
8. extractionis then extracted with ether
9. extractionThe ether extract
10. washis washed with hydrochloric acid solution (1N), sokium bicarbonate solution and brine
11. dry with materialthen dried over MgSO4
12. concentrationconcentrated

ORD record

ord-5f5e9003f1f44741b745e3dc41f0ca3c

Source dataset

uspto-grants-2003_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06635655B1