Dichloromethane → HCID 14279310, compound

Temperature

25 °C

To 50 g (0.26 moles) of 4-t-butyl-2,6-dimethylbenzoic acid in 250 ml methylene chloride was added 25 ml (0.34 mole) of thionyl chloride at 25° C. After stirring overnight at 25° C. the solvent and remaining thionyl chloride were evaporated in vacuo. The resulting white solid was dissolved in 50 ml tetrahydrofuran and added dropwise to 250 ml of methanol containing 2 ml of pyridine. After heating the reaction mixture to reflux for 30 minutes the solvents were evaporated in vacuo and the residue was dissolved in 200 ml ethyl acetate and 100 ml of water was added. The organic phase was separated and washed with 100 ml saturated aqueous sodium bicarbonate, 50 ml water and 25 ml brine; then dried over anhydrous magnesium sulfate and evaporated to an oil. The oil was distilled in vacuo at 104°-8° C. at 1.2 mm of mercury to obtain 43 g (81% yield) of the title compound.

1. customwere evaporated in vacuo
2. dissolutionThe resulting white solid was dissolved in 50 ml tetrahydrofuran
3. additionadded dropwise to 250 ml of methanol containing 2 ml of pyridine
4. temperatureAfter heating the reaction mixture
5. temperatureto reflux for 30 minutes the solvents
6. customwere evaporated in vacuo
7. dissolutionthe residue was dissolved in 200 ml ethyl acetate
8. addition100 ml of water was added
9. customThe organic phase was separated
10. washwashed with 100 ml saturated aqueous sodium bicarbonate, 50 ml water and 25 ml brine
11. dry with materialthen dried over anhydrous magnesium sulfate
12. customevaporated to an oil
13. distillationThe oil was distilled in vacuo at 104°-8° C. at 1.2 mm of mercury

ORD record

ord-7f150194bf1e4a6cb742a75fd455272c

Source dataset

uspto-grants-1988_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04777270