Hydrochloric Acid → HCID 10331962, compound

25 ml of 10% hydrogen chloride-methanol was added to 1.95 g (8.62 mmol) of 3-benzoylbenzoic acid and the mixture was stirred overnight at room temperature. The reaction mixture was concentrated under reduced pressure. The resulting residue was dissolved in ethyl acetate, washed with a sodium hydrogencarbonate aqueous solution and brine, and dried (MgSO4). The solvent was distilled off and the residue was dissolved in 20 ml of methanol. Under ice-cooling, 0.32 g (8,41 mmol) of sodium boronhydride was added thereto and the mixture was stirred for 30 minutes. After acetone and 1N hydrochloric acid were added, the reaction mixture was extracted twice with chloroform, the extract was washed with a sodium hydrogencarbonate aqueous solution, and dried (MgSO4). The solvent was distilled off to obtain 2.04 g (8.42 mmol) of methyl a-hydroxy-a-phenyl-m-toluate as a colorless oily substance. Its spectroscopic data are as follows:

1. concentrationThe reaction mixture was concentrated under reduced pressure
2. dissolutionThe resulting residue was dissolved in ethyl acetate
3. washwashed with a sodium hydrogencarbonate aqueous solution and brine
4. dry with materialdried (MgSO4)
5. distillationThe solvent was distilled off
6. dissolutionthe residue was dissolved in 20 ml of methanol
7. temperatureUnder ice-cooling
8. stirringthe mixture was stirred for 30 minutes
9. extractionthe reaction mixture was extracted twice with chloroform
10. washthe extract was washed with a sodium hydrogencarbonate aqueous solution
11. dry with materialdried (MgSO4)
12. distillationThe solvent was distilled off

ORD record

ord-ddf6cb34467f4b1284a7da76276a2d44

Source dataset

uspto-grants-2000_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06069149