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 for about 16 hours at room temperature. At the conclusion of this period, 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, and 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 3-(hydroxymethyl)benzoic acid (680 mg, 4.47 mmol, 88% yield) as a colorless powder. MS (ESI+)=153.10, (M+H)+.

1. customAt the conclusion of this period, the 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-e0c91deb8cbf47ff85279579a0be54d2

Source dataset

uspto-grants-2013_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08536198B2