2-(4-Chlorophenyl)-2-methylpropionic acid → 2-(4-Chlorophenyl)-2-methylpropanol

The 2-(4-chlorophenyl)-2-methyl-propionic acid (6.10 g, 30.7 mmol) was dissolved in 120 mL of dry THF at room temperature. A 70% w/w solution of Red-Al (28.25 mL, 0.101 mol) was added dropwise via syringe over 5 minutes (vigorous bubbling). The mixture was heated to reflux for three hours. The solution was cooled to 0 C and carefully quenched with the addition of saturated sodium tartrate solution (100 mL, violent hydrogen evolution) and 100 mL of water. The aqueous mixture was extracted with ethyl acetate, and the combined organic was washed with diluted NaHCO3 solution, then brine, separated, dried over MgSO4, filtered, and concentrated in vacuo to afford 2-(4-chlorophenyl)-2-methyl-propan-1-ol as a colorless oil (5.70 g, 99%). The material was used without purification. 1H NMR (CDCl3, 400 MHz) δ 7.32 (s, 5H), 3.62 (d, J=4.4 Hz, 2H), 1.33 (s, 6H), 1.23 (t, J=4.4 Hz, 1H).

1. custom(vigorous bubbling)
2. temperatureThe mixture was heated
3. temperatureto reflux for three hours
4. temperatureThe solution was cooled to 0 C
5. customcarefully quenched with the addition of saturated sodium tartrate solution (100 mL, violent hydrogen evolution) and 100 mL of water
6. extractionThe aqueous mixture was extracted with ethyl acetate
7. washthe combined organic was washed with diluted NaHCO3 solution
8. custombrine, separated
9. dry with materialdried over MgSO4
10. filtrationfiltered
11. concentrationconcentrated in vacuo

ORD record

ord-253a0a595d274589ab77cf1e7d1ca280

Source dataset

uspto-grants-2014_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08680114B2