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

Temperature

80 °C

To methyl 3-(hydroxymethyl)-4-isopropoxy-benzoate (180 mg, 0.8 mmol) in dioxane (2 mL) was added sodium hydroxide (2.1 mL of 1 M, 2.1 mmol) and the reaction mixture was heated at 80° C. for 50 minutes. The solvent was evaporated under reduced pressure. The residue was dissolved in water (10 mL) and washed with ethyl acetate (3×10 mL). The layers were separated and aqueous layer was acidified with hydrochloric acid. The aqueous layer was extracted with ethyl aceatate (3×10 mL). The organic layer was separated, dried over sodium sulfate, filtered and concentrated in vacuo to yield 3-(hydroxymethyl)-4-isopropoxy-benzoic acid (150 mg, 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 residue was dissolved in water (10 mL)
3. washwashed with ethyl acetate (3×10 mL)
4. customThe layers were separated
5. extractionThe aqueous layer was extracted with ethyl aceatate (3×10 mL)
6. customThe organic layer was separated
7. dry with materialdried over sodium sulfate
8. filtrationfiltered
9. concentrationconcentrated in vacuo

ORD record

ord-d63daa9c1ed14212ac744aab40e4ece3

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08828996B2