Water → 2-(2-Phenylethoxy)ethanol

Temperature

0 °C

Under nitrogen atmosphere, at 0° C., to a stirring mixture of LiAlH4 (0.93 g, 24.63 mmol) in dry Et2O (60 mL), 2-phenethyloxyacetic acid (1.1 g, 6.15 mmol) in dry Et2O (6 mL) was added dropwise. The mixture was left to react at rt for 4 h, then at 0° C. H2O (0.93 mL), 3.0 M KOH solution (0.93 mL) and H2O (3.12 mL) were very slowly added. The mixture was stirred at 0° C. for 1 h, filtered to remove the solid residue, and the organic phase dried over Na2SO4. The organic solution was again filtered and concentrated to dryness. The crude mixture was purified by column chromatography using a Teledyne ISCO apparatus, eluting with Cy:EtOAc (from 100:0 to 60:40) affording the title compound (0.69 g, 68%) as a colorless oil. 1H NMR (DMSO-d6): δ 2.81 (t, J=7.1 Hz, 2H), 3.40-3.44 (m, 2H), 3.45-3.51 (m, 2H), 3.60 (t, J=7.1 Hz, 2H), 4.55 (t, J=5.4 Hz, 1H), 7.15-7.30 (m, 5H).

1. additionwas added dropwise
2. waitThe mixture was left
3. customto react at rt for 4 h
4. customat 0° C
5. filtrationfiltered
6. customto remove the solid residue
7. dry with materialthe organic phase dried over Na2SO4
8. filtrationThe organic solution was again filtered
9. concentrationconcentrated to dryness
10. customThe crude mixture was purified by column chromatography
11. washeluting with Cy

ORD record

ord-539ce4dd420d4d3f87f9e9689d578dcd

Source dataset

uspto-grants-2016_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09353075B2