Sodium Hydroxide → 3-(Hydroxymethyl)-4-isopropoxybenzoic acid

Temperature

80 °C

To methyl 3-(hydroxymethyl)-4-isopropoxy-benzoate (180 mg, 0.80 mmol) and 1,4-dioxane (1.895 mL) was added sodium hydroxide (2.1 mL of 1.0 M, 2.1 mmol) and the mixture was heated at 80° C. for 50 minutes. The solvent was evaporated under reduced pressure. The crude mixture was dissolved in water (10 mL) and was washed with ethyl acetate (3×10 mL) which was discarded. The aqueous layer was acidified with hydrochloric acid. The aqueous layer was extracted with ethyl acetate (3×10 mL). The combined organics were dried over sodium sulfate, filtered and the solvent was evaporated under reduced pressure to yield 3-(hydroxymethyl)-4-isopropoxy-benzoic acid (89%) as a white solid. ESI-MS m/z calc. 210.2. found 211.3 (M+1)+; Retention time: 1.01 minutes (3 min run).

1. customThe solvent was evaporated under reduced pressure
2. dissolutionThe crude mixture was dissolved in water (10 mL)
3. washwas washed with ethyl acetate (3×10 mL) which
4. extractionThe aqueous layer was extracted with ethyl acetate (3×10 mL)
5. dry with materialThe combined organics were dried over sodium sulfate
6. filtrationfiltered
7. customthe solvent was evaporated under reduced pressure

ORD record

ord-29847f5b2d06470594462c09fda93123

Source dataset

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08598164B2