Methyl iodide → 1-Methylcyclohex-3-ene-1-carboxylic acid

Temperature

-78 °C

N-isopropylpropan-2-amine (50.1 g, 69.5 mL, 495.5 mmol) was dissolved in 50 mL of THF. To the solution was added n-butyllithium (174.4 mL of 2.5 M solution in hexanes, 436.0 mmol) at −78° C. The resulting solution was stirred for 30 minutes at −78° C. To the reaction was then added cyclohex-3-ene-1-carboxylic acid (25.0 g, 198.2 mmol) and the reaction was allowed to warm to 60° C. for 2 hrs. The reaction was cooled to room temp and iodomethane (29.5 g, 13.0 mL, 208.1 mmol) was added and the reaction was allowed to stir overnight and then quenched with 1 N HCl until the pH<4. The crude product was extracted into CH2Cl2 and water. The organic phase was concentrated in vacuo to a yellow oil (27 g) and used without further purification.

1. temperatureto warm to 60° C. for 2 hrs
2. temperatureThe reaction was cooled to room temp
3. stirringto stir overnight
4. customquenched with 1 N HCl until the pH<4
5. extractionThe crude product was extracted into CH2Cl2 and water
6. concentrationThe organic phase was concentrated in vacuo to a yellow oil (27 g)
7. customused without further purification

ORD record

ord-25682a58e0934f7cb8bcc37c8d69545f

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08829007B2