3-Hydroxybenzaldehyde → 3-(2,2,2-Trifluoroethoxy)benzaldehyde

Temperature

90 °C

Combine 3-hydroxybenzaldehyde (134.3 g), potassium carbonate (304.0 g), 2,2,2-trifluoroethyl p-toluenesulfonate (293.6 g) and dimethylformamide (2 L). Heat the mixture at 90° C. After 15 hours, cool to room temperature, pour on ice-water, and extract with dichloromethane. Combine the organic layers, wash with 1N sodium hydroxide, and then with water. Dry the organic phase over magnesium sulfate, filter, and concentrate to a residue. Dissolve residue in toluene (200 ml), Chromatograph on silica gel eluting sequentailly with toluene and then ethyl acetate to give a residue. Distill the reside under reduced pressure using a Claisen flask equipped with a Vigreux column gives title compound: bp 0.8 mm Hg, 84–85° C. Redistilling some fractions using a Claisen flask equipped with a Vigreux column and subsequently an adiabatic column filled with Rasching rings gives title compound: bp 0.9–1.0 mm Hg, 74–76° C.

1. temperaturecool to room temperature
2. additionpour on ice-water
3. extractionextract with dichloromethane
4. washwash with 1N sodium hydroxide
5. dry with materialDry the organic phase over magnesium sulfate
6. filtrationfilter
7. concentrationconcentrate to a residue
8. customDissolve residue in toluene (200 ml), Chromatograph on silica gel eluting sequentailly with toluene and then ethyl acetate to give a residue
9. distillationDistill the reside under reduced pressure
10. customequipped with a Vigreux column

ORD record

ord-8be9a1d9691a41088ff71a9a64aeff64

Source dataset

uspto-grants-2007_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07157488B2