4-Hydroxybiphenyl → 3-(4-Phenylphenoxy)-1-propanol

Temperature

0 °C

A solution of 4-phenylphenol (4.9 g, 29.0 mmol) and potassium tert-butoxide (3.64 g, 30.3 mmol) in THF (100 mL) was stirred at room temperature for 30 minutes. The solution was cooled at 0° C. and [1,3,2]dioxathiane 2,2-dioxide (Example 291, Step 5) (3.6 g, 26.34 mmol) in THF (25 mL) was added. The mixture was stirred at room temperature for 5 hours, and the solvent was removed under vacuum. The residue was dissolved in 6N HCl (15 mL) and heated at 100° C. for 16 hours. The mixture was cooled to room temperature, and the aqueous phase was extracted with ethyl acetate (3×30 mL). The combined organic layers were washed with H2O (3×25 mL) and brine (25 mL), dried (MgSO4), filtered, and concentrated to produce a white solid. 1H-NMR (200.15 MHz, CDCl3): d 7.57–7.49 (m, 4H), 7.45–7.37 (m, 3H), 6.98 (dd, 2H, J=6.72, 2.14), 4.17 (t, 2H, J=5.9), 3.88 (q, 2H, J=5.9), 2.07 (qn, 2H, J=5.9).

1. customthe solvent was removed under vacuum
2. dissolutionThe residue was dissolved in 6N HCl (15 mL)
3. temperatureheated at 100° C. for 16 hours
4. temperatureThe mixture was cooled to room temperature
5. extractionthe aqueous phase was extracted with ethyl acetate (3×30 mL)
6. washThe combined organic layers were washed with H2O (3×25 mL) and brine (25 mL)
7. dry with materialdried (MgSO4)
8. filtrationfiltered
9. concentrationconcentrated
10. customto produce a white solid

ORD record

ord-613ae9a2e23a41e6963997c392859ba7

Source dataset

uspto-grants-2007_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07192982B2