Carbon Dioxide → 2,4,6-Trimethoxybenzoic acid

To a stirred solution of 1,3,5-trimethoxybenzene (10.0 g, 59.4 mmol) in 150 mL of dry THF at 0° C. in nitrogen atmosphere was added 27.3 mL (68.31 mmol) of 2.5 M n-BuLi in hexane dropwise via syringe. The resulting solution was stirred at room temperature overnight. The mixture was cooled to -20° C. and 30 g of dry ice was added. Stirring was continued for 1 hr before hydrolysis with 200 mL of water. The mixture was evaporated under reduced pressure to remove THF. The aqueous phase was extracted with ether, acidified with hydrochloric acid to pH 3 and extracted with ethyl acetate. The organic layer was washed with brine, dried (MgSO4) and concentrated. The solid residue was washed with ether and dried in vacuo to give 6.7 g of the title compound: mp 152-153° C. dec (lit.: 147° C. dec.; Beilsteins, 10, 1988). 1H NMR (CDCl3): 6.16 (2 H, s), 3.91 (6 H, s), 3.86 (3 H, s).

1. temperatureThe mixture was cooled to -20° C.
2. stirringStirring
3. customThe mixture was evaporated under reduced pressure
4. customto remove THF
5. extractionThe aqueous phase was extracted with ether
6. extractionextracted with ethyl acetate
7. washThe organic layer was washed with brine
8. dry with materialdried (MgSO4)
9. concentrationconcentrated
10. washThe solid residue was washed with ether
11. customdried in vacuo

ORD record

ord-862738343ef74af6a9196b32e7cbdaa9

Source dataset

uspto-grants-2000_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06057315