Water → 2,4,6-Trifluorobenzyl alcohol

To a stirred solution of 4.1 grams (0.023 mole) of 2,4,6-trifluorobenzoic acid in 50 ml of anhydrous tetrahydrofuran, under a nitrogen atmosphere was added dropwise 4.0 grams (0.047 mole) of borane-tetrahydrofuran complex (as 46.6 ml of a 1.0 molar solution in tetrahydrofuran). The addition caused the reaction mixture to foam. Upon completion of addition the reaction mixture was stirred at ambient temperature for two hours, then was heated under reflux for one hour. The reaction mixture was cooled and 50 ml of water was cautiously added. The tetrahydrofuran was removed under reduced pressure and the residue washed into a separatory funnel with 100 ml of aqueous 2N sodium hydroxide. The mixture was extracted with three 100 ml portions of methylene chloride. The combined extracts were dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to give 3.2 grams of 2,4,6-trifluorophenylmethyl alcohol as an oil.

1. additionThe addition
2. additionUpon completion of addition the reaction mixture
3. temperaturewas heated
4. temperatureunder reflux for one hour
5. temperatureThe reaction mixture was cooled
6. customThe tetrahydrofuran was removed under reduced pressure
7. washthe residue washed into a separatory funnel with 100 ml of aqueous 2N sodium hydroxide
8. extractionThe mixture was extracted with three 100 ml portions of methylene chloride
9. dry with materialThe combined extracts were dried with magnesium sulfate
10. filtrationfiltered
11. concentrationThe filtrate was concentrated under reduced pressure

ORD record

ord-39d88c4fc7b14798adfa52d0ba5bafd2

Source dataset

uspto-grants-1988_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04758590