Sodium Hydroxide → Benzoic acid, 3-(hydroxymethyl)-

A solution of methyl 3-(hydroxymethyl)benzoate (845 mg, 5.09 mmol) in methanol (15 mL) was treated with 1 M NaOH (aq) (15.300 mL, 15.30 mmol), and the reaction was stirred overnight at room temperature. The methanol was removed under reduced pressure, and the remaining aqueous solution was washed 3× with 10 mL of diethyl ether. The aqueous phase was acidified to pH 1 with concentrated HCl, then extracted 3× with 20 mL of ethyl acetate. The combined organic phases were washed with brine, dried over sodium sulfate, and concentrated in-vacuo to yield the title compound (680 mg, 4.47 mmol, 88% yield) as a colorless powder. MS (ESI+)=153.10, (M+H)+.

1. customThe methanol was removed under reduced pressure
2. washthe remaining aqueous solution was washed 3× with 10 mL of diethyl ether
3. extractionextracted 3× with 20 mL of ethyl acetate
4. washThe combined organic phases were washed with brine
5. dry with materialdried over sodium sulfate
6. concentrationconcentrated in-vacuo

ORD record

ord-444632921fcf42bf9732c28289868c44

Source dataset

uspto-grants-2011_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07985861B2