Reaktion #1533564

Reaktionsgleichung

methyl 2-methyl-2,3-dihydrobenzofuran-2-carboxylate

2-Methyl-2,3-dihydrobenzofuran-2-carboxylic acid, methyl ester

potassium hydroxide

→

title compound

2-Methyl-2,3-dihydrobenzofuran-2-carboxylic acid

Lösungsmittel

dimethylsulfoxide

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe reaction mixture was partitioned between ether (50 mL) and 1 M hydrochloric acid (50 mL)
2. 2
   SonstigeThe organic layer was separated
3. 3
   Extraktionthe aqueous layer extracted with ether (3×50 mL)
4. 4
   TrocknenThe combined organic extracts were dried over anhydrous sodium sulfate
5. 5
   Filtrationfiltered
6. 6
   Einengenconcentrated to dryness

Vorschrift

To a solution of methyl 2-methyl-2,3-dihydrobenzofuran-2-carboxylate (Step B, 0.22 g, 1.1 mmol) in 5 mL of dimethylsulfoxide was added potassium hydroxide (0.64 g, 11 mmol) in 0.5 mL of water. After stirring at room temperature for 1 h, the reaction mixture was partitioned between ether (50 mL) and 1 M hydrochloric acid (50 mL). The organic layer was separated and the aqueous layer extracted with ether (3×50 mL). The combined organic extracts were dried over anhydrous sodium sulfate, filtered, and concentrated to dryness to give the title compound. 1H NMR (500 MHz, CD3OD): δ 7.17 (d, 1H), 7.12 (t, 1H), 6.86 (t, 1H), 6.79 (d, 1H), 3.60 (d, 1H), 3.18 (d, 1H), 1.67 (s, 3H).

Quelle