Methyl iodide → 5-Chloro-o-anisic acid

A mixture of 17.2 g (0.1 mole) of 5-chlorosalicylic acid, 28 g. of potassium carbonate, 25 ml. of methyl iodide, and 100 ml. of N,N-dimethylformamide was heated at 60° C. for 16 hours. The mixture was diluted with water and extracted with diethyl ether. The ether extracts were evaporated and the residue dissolved in benzene. The resulting solution was washed with 5 percent sodium hydroxide solution and dried over magnesium sulfate. Evaporation provided a residue which was mixed with 100 ml. of ethanol and 100 ml. of 10 percent sodium hydroxide solution and heated at reflux for two hours. The mixture was evaporated to provide a residue which was washed with 5 percent hydrochloric acid solution, and recrystallized from carbon tetrachloride to provide white solid 5-chloro-2-methoxybenzoic acid, m.p. 95°98° C.

1. extractionextracted with diethyl ether
2. customThe ether extracts were evaporated
3. dissolutionthe residue dissolved in benzene
4. washThe resulting solution was washed with 5 percent sodium hydroxide solution
5. dry with materialdried over magnesium sulfate
6. customEvaporation
7. customprovided a residue which
8. additionwas mixed with 100 ml
9. temperatureat reflux for two hours
10. customThe mixture was evaporated
11. customto provide a residue which
12. washwas washed with 5 percent hydrochloric acid solution
13. customrecrystallized from carbon tetrachloride

ORD record

ord-4128d414a9f84dc8bd9b05c04023be4a

Source dataset

uspto-grants-1984_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04474792