Benzene → HCID 13280229, compound

Temperature

7 °C

Under an argon atmosphere benzene (335 ml, 3.74 mol) and aluminum trichloride (90.78 g, 0.68 mol) were introduced into a 1 liter three necked round bottomed flask fitted with a magnetic stirring apparatus, an addition funnel and a reflux condenser. The stirred orange mixture was cooled to 7° C. and tigloyl chloride (33) (40 g, 0.34 mol) was added dropwise via an addition funnel. After completion of the addition, the mixture was allowed to come to room temperature and then refluxed overnight. Then the reaction mixture was allowed to come to room temperature and poured onto mixture of ice (300 g) and conc. HCl (50 ml). The organic layer was separated and washed with a saturated solution of sodium bicarbonate (3×100 ml), then dried over magnesium sulfate and filtered. The excess benzene was removed under reduced pressure to afford (34) (50.02 g, 92%) as a yellow liquid. The 1H NMR spectrum was identical with the literature (T. E. Ready, J. C. W. Chien, M. D. Rausch, J. Org. Chem. 1999 583, 11-27; J. Sarrazin, A. Tallec, Tetrahedron Letters, 1977, 18, 1579-1582; M. Hiscock, G. B. Porter, J. Chem. Soc. (B), 1971, 1631-1634).

1. customfitted with a magnetic stirring apparatus, an addition funnel and a reflux condenser
2. additionAfter completion of the addition
3. customto come to room temperature
4. temperaturerefluxed overnight
5. customto come to room temperature
6. customThe organic layer was separated
7. washwashed with a saturated solution of sodium bicarbonate (3×100 ml)
8. dry with materialdried over magnesium sulfate
9. filtrationfiltered
10. customThe excess benzene was removed under reduced pressure

ORD record

ord-e870464a814240fbb8fc098b76aa91ea

Source dataset

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08969624B2