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 completion of 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 completion of 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), sodium 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 completion of addition
2. customthe cold bath is removed
3. concentrationThe resulting solution is concentrated under vacuum
4. additionthe residue added slowly to
5. additionOn completion of addition
6. stirringthe reaction mixture is 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), sodium bicarbonate solution and brine
11. dry with materialthen dried over MgSO4
12. concentrationconcentrated

ORD record

ord-643b09a1533b484382ce8589f4fe928f

Source dataset

uspto-grants-2006_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07005440B1