Iodoethane → 2-Methyl-4-ethylaminobenzaldehyde

A mixture of purified 2-methyl-4-acetamidobenzaldehyde (9.6 g, 0.054 mole), ethyl iodide (10 ml, 0.125 mole), and 50 ml of tetrahydrofaran was warmed to about 300 with stirring under a nitrogen atmosphere. Solid potassium t-butoxide (6.25 g, 0.056 mole) was added and the mixture was stirred for 2.5 hr at 30°. The mixture was concentrated under vacuum at 50° on a rotary evaporator to a syrup. The syrup was dissolved in methanol (30 ml) before adding water (20 ml) and then sodium hydroxide (5 g, 0.125 mole) to the mixture. After heating the mixture to reflux temperature for 30 min, it was cooled to rt and water (120 ml) was added. Solid product precipitated on stirring over night. After filtering and drying, 5.1 g (58%) of 2-methyl-4-ethylaminobenzaldehyde was obtained.

1. temperatureof tetrahydrofaran was warmed to about 300
2. stirringthe mixture was stirred for 2.5 hr at 30°
3. concentrationThe mixture was concentrated under vacuum at 50° on a rotary evaporator to a syrup
4. dissolutionThe syrup was dissolved in methanol (30 ml)
5. additionbefore adding water (20 ml)
6. temperatureAfter heating the mixture
7. temperatureto reflux temperature for 30 min
8. customSolid product precipitated
9. stirringon stirring over night
10. filtrationAfter filtering
11. customdrying

ORD record

ord-9fe1427852194cb29956f66beabdc7be

Source dataset

uspto-grants-2001_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06172260B2