Dimethylformamide → HCID 58551495, compound

Temperature

80 °C

Methyl 2,4-dihydroxy-3-methyl-benzoate (193 mg, 1.06 mmol) was dissolved in DMF (1 mL) containing cesium carbonate (1.03 g, 3.18 mmol). Iodoethane (847 μL, 10.6 mmol) was added and the reaction mixture was allowed to stir for 86 hours. The reaction mixture was then filtered and evaporated to dryness. The crude material was then dissolved in a mixture of dioxane (2 mL) and sodium hydroxide (1.1 mL of 1.0 M, 1.1 mmol). The reaction mixture was then heated at 80° C. for 75 minutes. The dioxane was evaporated to dryness and the reaction mixture was made acidic with 4M hydrochloric acid. The aqueous layer was extracted 3 times with ethyl acetate. The combined ethyl acetate extracts were then dried over sodium sulfate, filtered, and evaporated to dryness to yield 2,4-diethoxy-3-methyl-benzoic acid (189 mg, 80%) as a pale yellow solid which was used without further purification. 1H NMR (400 MHz, DMSO) δ 12.37 (s, 1H), 7.62 (d, J=8.7 Hz, 1H), 6.79 (d, J=8.8 Hz, 1H), 4.08 (q, J=6.9 Hz, 2H), 3.87 (q, J=7.0 Hz, 2H), 2.06 (s, 3H), 1.36 (t, J=6.9 Hz, 3H), 1.30 (t, J=7.0 Hz, 3H).

1. filtrationThe reaction mixture was then filtered
2. customevaporated to dryness
3. customThe dioxane was evaporated to dryness
4. extractionThe aqueous layer was extracted 3 times with ethyl acetate
5. dry with materialThe combined ethyl acetate extracts were then dried over sodium sulfate
6. filtrationfiltered
7. customevaporated to dryness

ORD record

ord-5b2d7baa48a44a96b54898f60d879368

Source dataset

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08598164B2