2-Chloroethanol → [4-(2-Hydroxyethoxy)phenyl](phenyl)methanone

To a solution of 4-hydroxybenzophenone (6.0 g, 29.7 mmol) in acetone (50 mL) were added K2CO3 (12.3 g, 89.0 mmol) and 2-chloroethanol (4.0 mL, 59.3 mmol), followed by addition of NaI (4.50 g, 29.7 mmol). The reaction mixture was refluxed under nitrogen overnight. The mixture was cooled to room temperature. The white solid was filtered off and washed with acetone (100 mL). The filtrate was concentrated to a brown oil residue with some white solid. EtOAc (200 mL) was added, the white solid was filtered off and then washed with 50 mL of EtOAc. The filtrate was washed with 1 N NaOH, water, brine and dried over Na2SO4. Concentration afforded a pale yellow oil which was further purified by chromatography on a silica gel column eluted with a gradient from hexanes to 60% EtOAc:hexanes to give 5 as a white solid (1.52 g, 21%). 1H NMR (400 MHz, CDCl3): δ 4.00-4.05 (m, 2H), 4.15-4.20 (m, 2H), 6.98 (d, J=8.7 Hz, 2H), 7.45-7.50 (m, 2H), 7.55-7.60 (m, 1H), 7.75 (d, J=7.1 Hz, 2H), 7.83 (d, J=8.8 Hz, 2H).

1. temperatureThe reaction mixture was refluxed under nitrogen overnight
2. filtrationThe white solid was filtered off
3. washwashed with acetone (100 mL)
4. concentrationThe filtrate was concentrated to a brown oil residue with some white solid
5. additionEtOAc (200 mL) was added
6. filtrationthe white solid was filtered off
7. washwashed with 50 mL of EtOAc
8. washThe filtrate was washed with 1 N NaOH, water, brine
9. dry with materialdried over Na2SO4
10. concentrationConcentration
11. customafforded a pale yellow oil which
12. customwas further purified by chromatography on a silica gel column
13. washeluted with a gradient from hexanes to 60% EtOAc

ORD record

ord-510e3c58af3b442e9ee0ec7e3ef01ec8

Source dataset

uspto-grants-2010_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07723393B2