Potassium Hydroxide → 4-Hydroxy-4-[3,4-dimethoxy-2-(1-methylethyl)phenyl]-3-methylbut-2-enoic Acid

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Reaction Steps

Compound 8 (9.00 g, 27.9 mmol) was dissolved in 100 mL of ethanol with 3 g of KOH and refluxed for 1 h. The mixture was poured onto 100 g of ice with 25 ml of 6M HCL and stirred for 24 h. The white solid was filtered, washed with water, dried and recrystallized from ether/petroleum ether to give 7.38 g (25.1 mmol, 90%) of 9 as white plates: mp 154°-155° C.; IR 3411 (OH), 1694 (carbonyl), 1644 (alkene) cm-1 ; 1H NMR δ 1.38 (d, J=7.0 Hz, 6 H), 2.00 (s, 3 H), 3.44 (br s, 1 H), 3.85 (s, 6 H), 5.41 (s, 1H), 6.33 (s, 1 H), 6.75 (d, J=8.6 Hz, 1 H), 6.92 (d, J=7.1 Hz, 1 H). Anal. (C6H22 O5) C,H.

Provenance & Evidence