Water → 4-chloro-2-ethylBenzoic acid

To a yellow solution of 2,2,6,6-TMPH (5.45 g, 38.69 mmol) in THF (6 mL) was added n-BuLi (16 mL) slowly at −78° C. under protection of nitrogen, thereto, the mixture was warmed up to room temperature, stirred at this temperature for an hour, and then cooled to −78° C. again, a solution of 4-chloro-2-methylbenzoic acid (3.0 g, 17.58 mmol) in THF (30 mL) was added slowly, kept stirring at this temperature for an hour, added MeI (5.49 g, 38.69 mmol) solution (in 20 mL THF), the mixture above was then stirred overnight at room temperature. LCMS showed the completion of the reaction, added water, the mixture was then washed with ethyl acetate, the aqueous phase was acidified to pH=1, extracted with ethyl acetate twice, and concentrated the organic phase, washed the residue with PE/EA=1/1 to give 1.5 g of the title compound (46%).

1. temperaturecooled to −78° C. again
2. stirringkept stirring at this temperature for an hour
3. stirringthe mixture above was then stirred overnight at room temperature
4. customthe completion of the reaction
5. washthe mixture was then washed with ethyl acetate
6. extractionextracted with ethyl acetate twice
7. concentrationconcentrated the organic phase
8. washwashed the residue with PE/EA=1/1

ORD record

ord-a8fa18e2a6a443c6b0750be395871446

Source dataset

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08987461B2