Hydrochloric Acid → 2,6-Dimethyl-2-(2-methyl-allyl)-cyclohexanone

Temperature

60 °C

2,6-Dimethyl-cyclohexanone (1 kg, 4 mol), trimethyl orthoformate (TMOF, 880 g), and methanol (800 mL) were charged to a 5 L reaction flask. HCl was added quickly. Reaction exothermed and the temperature increased from 14° C. to 20° C. The reaction mixture was heated to 60° C. and aged for 7 hours. When the reaction was about 75% complete, the reaction mixture was quenched with NaOCH3 (25%, 25 g), heated to 90° C., and applied to a Dean-Stark trap. The reaction mixture was then cooled to room temperature followed by sequential addition of methallyl alcohol (1.25 Kg, 8.5 moles), HOAc (50 g), and methane sulfonic acid (MSA, 10 g). The resulting mixture was heated to 110° C., applied to a Bidwell-Sterling trap, and aged for 4 hours until gas chromatograph analysis indicated that the reaction was 95% completed. The reaction mixture was then cooled and washed with saturated sodium carbonate solution (3 L) to provide the crude product 2,6-dimethyl-2-(2-methyl-allyl)-cyclohexanone.

1. customReaction
2. temperaturethe temperature increased from 14° C. to 20° C
3. customthe reaction mixture was quenched with NaOCH3 (25%, 25 g)
4. temperatureheated to 90° C.
5. temperatureThe reaction mixture was then cooled to room temperature
6. temperatureThe resulting mixture was heated to 110° C.
7. temperatureThe reaction mixture was then cooled
8. washwashed with saturated sodium carbonate solution (3 L)

ORD record

ord-ebb7939237924832b188d50182c86207

Source dataset

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09181514B2