Iodoethane → HCID 53442006, compound

To a solution of 3-hydroxy-4-iodo-benzoic acid (4 g, 15.15 mmol) in 2-butanone (100 mL) were added potassium carbonate (20 g, finely ground) and ethyl iodide (4.85 mL). The mixture was stirred at reflux overnight. Upon cooling to room temperature, the solids were filtered off, and the filtrate was concentrated. The residue was partitioned between ethyl acetate and water, and the organic layer was washed with 10% sodium carbonate solution, brine, and concentrated. The residue reconstituted in methanol. 1.0 M sodium hydroxide was added giving a cloudy solution. Tetrahydrofuran was added to clarity and the mixture stirred at room temperature for one hour. The volatiles were evaporated and the residue was dissolved in water. It was washed once with diethyl ether and then acidified with 37% hydrochloric acid to precipitate a white solid. The solid was filtered, washed with water and dried in a vacuum oven to give 3-ethoxy-4-iodo-benzoic acid (2.73 g, 62%). LC-MS: 293 [(M+H)+].

1. temperatureat reflux overnight
2. filtrationthe solids were filtered off
3. concentrationthe filtrate was concentrated
4. customThe residue was partitioned between ethyl acetate and water
5. washthe organic layer was washed with 10% sodium carbonate solution, brine
6. concentrationconcentrated
7. addition1.0 M sodium hydroxide was added
8. customgiving a cloudy solution
9. stirringthe mixture stirred at room temperature for one hour
10. customThe volatiles were evaporated
11. dissolutionthe residue was dissolved in water
12. washIt was washed once with diethyl ether
13. customto precipitate a white solid
14. filtrationThe solid was filtered
15. washwashed with water
16. customdried in a vacuum oven

ORD record

ord-773a0b84220a45b08c30bda1ce2e10af

Source dataset

uspto-grants-2009_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07579368B2