Phthalic Anhydride → 3-Butylcyclohexanone

To 30 ml of anhydrous diethyl ether were added 3.8 g (20 mmol) of cuprous iodide and 4.0 g (20 mmol) of tri-n-butylphosphine, and the mixture was stirred for about 1 hour at room temperature in an atmosphere of nitrogen and then cooled to -78° C. Then, 25.6 ml (40 mmol) of a 15 % by weight hexane solution of n-butyllithium was added, and the mixture was stirred for 30 minutes, and 1.92 g (20 mmol) of 2-cyclohexenone was added. The mixture was further stirred for 1 hour at -78° C. Then, 5 ml of hexamethylphosphoric tiramide was added, and the mixture was stirred for about 10 minutes. Phthalic anhydride (2.96 g, 20 mmol) was further added, and the mixture was stirred for 3 hours at room temperature. After the reaction, a solution of 4 g (100 mmol) of sodium hydroxide in 50 ml of water was added, and the mixture was stirred for about 1 hour. It was extracted with ether, washed, and dried to afford 6.22 g of a crude product. The crude product was distilled to afford 1.62 g (10.5 mmol) of 3-n-butylcyclohexanone in a yield of 53%.

1. temperaturecooled to -78° C
2. stirringthe mixture was stirred for 30 minutes
3. stirringThe mixture was further stirred for 1 hour at -78° C
4. additionThen, 5 ml of hexamethylphosphoric tiramide was added
5. stirringthe mixture was stirred for about 10 minutes
6. stirringthe mixture was stirred for 3 hours at room temperature
7. customAfter the reaction
8. stirringthe mixture was stirred for about 1 hour
9. extractionIt was extracted with ether
10. washwashed
11. customdried
12. customto afford 6.22 g of a crude product
13. distillationThe crude product was distilled

ORD record

ord-02cc188640d848deaa2c2349341f38ee

Source dataset

uspto-grants-1977_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04009196