m-Phenylenediacetic acid → 2-[3-(2-Hydroxyethyl)phenyl]ethanol

Temperatur

0 °C

2,2′-(1,3-Phenylene)diacetic acid (1.000 g, 5.15 mmol), dissolved in anhydrous tetrahydrofuran (15 mL) was cooled at 0° C. in an ice bath and then added with lithium aluminum hydride (0.5860 g, 15.45 mmol). The reaction mixture was stirred at 0° C. for 3 h, and finally quenched by addition of hydrochloric acid (1N) until pH=7. The solution was filtered through filter paper, and extracted with ethyl acetate (15 mL×2). The organic layer was washed with brine (15 mL×2), dried over sodium sulfate, filtered and concentrated to dryness. The residue so obtained was purified by silica gel column chromatography eluting with a gradient of ethyl acetate in hexanes (50%-80%) to furnish the desired product. Yield 61%.

1. customfinally quenched by addition of hydrochloric acid (1N) until pH=7
2. filtrationThe solution was filtered
3. filtrationthrough filter paper
4. extractionextracted with ethyl acetate (15 mL×2)
5. washThe organic layer was washed with brine (15 mL×2)
6. dry with materialdried over sodium sulfate
7. filtrationfiltered
8. concentrationconcentrated to dryness
9. customThe residue so obtained
10. customwas purified by silica gel column chromatography
11. washeluting with a gradient of ethyl acetate in hexanes (50%-80%)

ORD-Eintrag

ord-6ac6b2a1093a4606be05d56a46e6a2b5

Quelldatensatz

uspto-grants-2013_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08530520B2