Ethanol → HCID 9903805, compound

Participants

Reaction Conditions

Reaction Steps

To 112.0 g (0.38 mol) of methyl 4-dodecylpyrrole-2-carboxylate prepared in Example 35 were added 1.45 liters of ethanol, 1.45 liters of water and 31.0 g (0.74 mol) of 95% sodium hydroxide, and the whole was heated under reflux for 2 hours. At 80° C., 1.45 liters of hot water was added and, at the same temperature, 6N sulfuric acid was added gradually to adjust the reaction solution to pH 2. After cooling the mixture to 45° C., precipitated crystals were filtered and washed with water. The crystals were dissolved in 4 liters of tetrahydrofuran, and the solution was washed twice with 1 liter of a saturated solution of sodium chloride and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure to give crystals, which were then recrystallized from a mixed solvent 600 ml of tetrahydrofurn and 600 ml of hexane to obtain 92.6 g (87% yield) of 4-dodecylpyrrole- 2-carboxylic acid as white crystals, m.p. 152°-153° C.

Provenance & Evidence