Hydrochloric Acid → 2-(4-chlorophenyl)-5,5-dimethyl-1-Cyclohexene-1-carboxaldehyde

The solution from EXAMPLE 3 was slowly treated with 2N HCl (240 mL), maintaining an internal temperature below 20° C. The contents were mixed at 20° C. for 10-12 hours, and the mixture was monitored by GC analysis. Isopropyl acetate (130 mL) was charged to the reaction mixture, and the layers were mixed and separated. The organic layer was washed with water (45 mL), 1% aqueous NaHCO3 (45 mL), and 20% aqueous NaCl (2×45 mL). The product mixture was azeotropically dried through a solvent exchange with toluene (125 g) to obtain a 32% solution of the title compound. 1H NMR (400 MHz, DMSO-d6) δ 0.95 (s, 6 H) 1.48 (t, J=6.45 Hz, 2 H) 2.03 (t, J=1.92 Hz, 2 H) 2.53-2.57 (m, J=6.38, 6.38, 2.20, 2.06 Hz, 2 H) 7.36 (ddd, J=8.75, 2.54, 2.30 Hz, 2 H) 7.47 (ddd, J=8.78, 2.54, 2.26 Hz, 2 H) 9.37 (s, 1 H) ppm. Mass Spec: DCI/NH3 M+1=248 amu; M+NH3=266 amu.

1. temperaturemaintaining an internal temperature below 20° C
2. additionThe contents were mixed at 20° C. for 10-12 hours
3. additionthe layers were mixed
4. customseparated
5. washThe organic layer was washed with water (45 mL), 1% aqueous NaHCO3 (45 mL), and 20% aqueous NaCl (2×45 mL)
6. dry with materialThe product mixture was azeotropically dried through a solvent exchange with toluene (125 g)

ORD record

ord-e16225fd1f0948aeb7988c6789f9ce74

Source dataset

uspto-grants-2012_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08168784B2