Alpha-Methylstyrene → 2-Phenylpropane-1,2-diol

To a solution of in prop-1-en-2-ylbenzene (commercially available from Sigma-Aldrich, Milwaukee, Wis.) (2 g, 16.9 mmol) in a THF (20 mL): H2O (10 mL) mixture were added N-methylmorpholine N-oxide (1.98 g, 16.9 mmol) and osmium tetroxide (429.90 mg, 1.6 mmol) at 0° C. The resulting reaction mixture was stirred for 2 hours at ambient temperature. After completion of reaction (monitored by TLC (TLC eluent: 30% EtOAc in petroleum ether)), the reaction mixture was diluted with water and extracted with EtOAc. The organic layers were combined and washed with water, washed with saturated NaCl solution, and dried on anhydrous Na2SO4. Then the organic layer was filtered and concentrated under vacuum to provide a residue which was purified by column chromatography eluting with 50-60% EtOAc in hexane to afford 2-phenylpropane-1,2-diol, 1.5 g (58.25%) as a colorless liquid. 1H NMR (400 MHz, DMSO-d6): δ 7.45-7.43 (m, 2H), 7.30-7.26 (m, 2H), 7.20-7.16 (m, 1H), 4.86 (s, 1H), 4.68 (t, J=6 Hz, 1H), 3.39 (d, J=6 Hz, 1H), 1.38 (s, 3H). (no MS ionization).

1. customThe resulting reaction mixture
2. extractionextracted with EtOAc
3. washwashed with water
4. washwashed with saturated NaCl solution
5. dry with materialdried on anhydrous Na2SO4
6. filtrationThen the organic layer was filtered
7. concentrationconcentrated under vacuum
8. customto provide a residue which
9. customwas purified by column chromatography
10. washeluting with 50-60% EtOAc in hexane

ORD record

ord-e1badc3e7b4a465cb24a9b7dc65d17c4

Source dataset

uspto-grants-2016_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09340549B2