Hydroxypropiophenone → (1S)-1-phenylpropane-1,3-diol

Temperature

30 °C

In a 500 ml stainless steel-made autoclave were charged 65 g (400 mmole) of 3-phenyl-3-oxopropanol and 550 mg (0.4 mmole) of [RuI(p-cymene)((R)-BINAP)]I3 synthesized in Example 1 in a nitrogen atmosphere, and 300 ml of methanol was added thereto, followed by stirring the mixture at 30° C. for 20 hours under a hydrogen pressure of 30 atm. The reaction mixture was concentrated and subjected to silica gel column chromatography (eluent: hexane/isopropanol=9/l by volume) to eliminate the complex. The obtained hydrogenation product was dissolved in a 6-fold amount of diisopropyl ether by heating and allowed to stand at 0° C. for 24 hours. The resulting precipitate was collected by filtration and dried (room temperature, 1 mmHg), and 45.5 g of (1S)-phenyl-1,3-propanediol was obtained as a colorless crystal (percent yield: 70.0%).

1. additionwas added
2. concentrationThe reaction mixture was concentrated
3. dissolutionThe obtained hydrogenation product was dissolved in a 6-fold amount of diisopropyl ether
4. temperatureby heating
5. waitto stand at 0° C. for 24 hours
6. filtrationThe resulting precipitate was collected by filtration
7. customdried (room temperature, 1 mmHg)

ORD record

ord-d12aa51b0e66491494e2677c22bcb4cd

Source dataset

uspto-grants-1994_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05324870