Dichloromethane → Chloromethyl 2-(4-(4-chlorobenzoyl)phenoxy)-2-methylpropanoate

A mixture of 2-(4-(4-chlorobenzoyl)phenoxy)-2-methylpropanoic acid (10.0 g, 31.4 mmol), sodium bicarbonate (13.2 g, 47.1 mmol, 1.5 eq) and tetrabutylammonium hydrogensulfate (2.1 g, 6.3 mmol, 0.2 eq) in water (150 mL) was stirred at room temperature for 15 min. Dichloromethane (150 mL) was added and the mixture was cooled in ice. Chloromethyl sulfochloridate (4.2 mL, 47.1 mmol, 1.5 eq) was added and the mixture was stirred overnight at room temperature. The layers were separated, the organic phase was washed with water (50 mL) and brine, then dried over sodium sulfate. The drying agent was filtered off and the solution was concentrated by rotary evaporation to leave a thick oil. Hexane (50 mL) and seeds were added and rotary evaporation was continued at room temperature to leave chloromethyl 2-(4-(4-chlorobenzoyl)phenoxy)-2-methylpropanoate 1 as a white solid (11.6 g, 101% yield). 1H-NMR (CDCl3) δ 7.73 (d, 2 H), 7.70 (d, 2 H), 7.44 (d, 2 H), 6.87 (d, 2 H), 5.77, (s, 2 H), 1.70 (s, 6 H) ppm.

1. temperaturethe mixture was cooled in ice
2. additionChloromethyl sulfochloridate (4.2 mL, 47.1 mmol, 1.5 eq) was added
3. stirringthe mixture was stirred overnight at room temperature
4. customThe layers were separated
5. washthe organic phase was washed with water (50 mL) and brine
6. dry with materialdried over sodium sulfate
7. filtrationThe drying agent was filtered off
8. concentrationthe solution was concentrated by rotary evaporation
9. customto leave a thick oil
10. customrotary evaporation
11. customwas continued at room temperature

ORD-Eintrag

ord-37e1aed844594d4e9253087802b89949

Quelldatensatz

uspto-grants-2015_05

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09024069B2