Methyl iodide → 2-Isopropylanisole

To a solution of 2-isopropylphenol (30 g, 220.3 mmol) in CH2Cl2 (300 mL) was added tetrabutylammonium hydrogen sulfate (7.5 g, 22.1 mmol). After the entire solid was dissolved, a solution of potassium hydroxide (61.8 g, 1.1 mol in 300 mL H2O) was added to the previous mixture. After 15 minutes of stirring, methyl iodide (47 g, 20.6 mL, 331 mmol) was added. The mixture was left to stir overnight (ca. 15 hours). The organic layer was separated and then washed with brine (2×100 mL), dried (Na2SO4), filtered and concentrated in vacuo. The solid material in the concentrate was removed by filtration. The precipitate was washed with hexane (100 mL). The filtrate was concentrated in vacuo to give 32.15 g of yellow oil as a crude product. The crude product was filtered through a pad of silica gel (250 g) and washed with 5% EtOAc in hexane to give 30.7 g (93%) of compound 1a as a colorless oil.

1. dissolutionAfter the entire solid was dissolved
2. waitThe mixture was left
3. stirringto stir overnight (ca. 15 hours)
4. customThe organic layer was separated
5. washwashed with brine (2×100 mL)
6. dry with materialdried (Na2SO4)
7. filtrationfiltered
8. concentrationconcentrated in vacuo
9. customThe solid material in the concentrate was removed by filtration
10. washThe precipitate was washed with hexane (100 mL)
11. concentrationThe filtrate was concentrated in vacuo

ORD record

ord-a63beb256fa54e15b1ab1d9d7ebdf694

Source dataset

uspto-grants-2004_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06747048B2