Hydrochloric Acid → (2-Ethoxy-3-isopropylphenyl)methanol

Temperature

0 °C

Diisobutylaluminum lithium hydride (55.0 mL of a 1.0 M in hexanes, 55.0 mmol) was added drop-wise to an ice-cold solution of 2-ethoxy-3-isopropylbenzoic acid propyl ester (4.34 g, 18.3 mmol) in THF (40 mL). After the addition was complete, the ice bath was removed and reaction mixture was stirred for 18 h. The reaction was cooled to 0° C. and HCl (1N, 275 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 (3.73 g, quantitative) as a light yellow oil: 1H NMR (300 MHz, DMSO-d6) δ 7.24 (d, J=5.7 Hz, 1H), 7.16 (d, J=1.7 Hz, 1H), 7.07 (t, J=7.5 Hz, 1H), 5.02 (t, J=5.6 Hz, 1H), 4.52 (d, J=−5.6 Hz, 2H), 3.77 (q, J=7.0 Hz, 2H), 3.32-3.25 (m, 1H), 1.33 (t, J=6.9 Hz, 3H), 1.16 (d, J=6.9, 6H).

1. additionAfter the addition
2. customthe ice bath was removed
3. customreaction mixture
4. extractionThe mixture was extracted with EtOAc (3×150 mL)
5. washThe combined organics were washed with brine (2×200 mL)
6. dry with materialdried (Na2SO4)
7. concentrationconcentrated

ORD record

ord-e40766bdcb514dfa8e34dd1453ee73c8

Source dataset

uspto-grants-2013_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08450307B2