Lithium diisobutylaluminum hydride → (3-Isopropyl-2-propoxyphenyl)methanol

Diisobutylaluminum lithium hydride (40.8 mL of a 1.0 M in hexanes, 40.8 mmol) was added dropwise to an ice-cold solution of 3-isopropyl-2-propoxybenzoic acid propyl ester (3.60 g, 13.6 mmol) in THF (30 mL). After the addition was complete, the ice bath was removed and the reaction mixture was stirred at ambient temperature for 18 h. The reaction was cooled to 0° C. and HCl (1N, 180 mL) was added until all the resulting solids returned to solution. The mixture was extracted with EtOAc (3×150 mL). The combined organics were washed with brine (2×200 mL), dried (Na2SO4) and concentrated to yield the title compound (2.76 g, 97%) as a yellow oil: 1H NMR (300 MHz, DMSO-d6) δ 7.25 (d, J=6.3 Hz, 1H), 7.17 (d, J=5.9 Hz, 1H), 7.10 (t, J=7.5 Hz, 1H), 5.02 (t, J=5.6 Hz, 1H), 4.52 (d, J=5.5 Hz, 2H), 3.68 (t, J=6.4 Hz, 2H), 3.32-3.25 (m, 1H), 1.77-1.70 (m, 2H), 1.16 (d, J=6.9, 6H), 1.02 (t, J=7.3 Hz, 3H).

1. additionAfter the addition
2. customthe ice bath was removed
3. temperatureThe reaction was cooled to 0° C.
4. additionHCl (1N, 180 mL) was added until all the resulting solids
5. extractionThe mixture was extracted with EtOAc (3×150 mL)
6. washThe combined organics were washed with brine (2×200 mL)
7. dry with materialdried (Na2SO4)
8. concentrationconcentrated

ORD record

ord-7f63b361853b4856abdfa2a76804a064

Source dataset

uspto-grants-2011_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07879872B2