[C:1]1(C)C=CC(S(O)(=O)=O)=CC=1.[OH:12][C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][CH:21]=1)[CH:18]([C:22]([OH:24])=[O:23])[CH2:17][CH2:16]2>CO>[OH:12][C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][CH:21]=1)[CH:18]([C:22]([O:24][CH3:1])=[O:23])[CH2:17][CH2:16]2In a 20-liter reactor with a mechanical stirrer, 1.6 kg of 2,3-dihydro-5-hydroxy-1H-inden-1-carboxylic acid were dissolved with 7.2 l of absolute methanol, 9 g of p-toluenesulphonic acid were added and then refluxed under stirring in oil bath heated at 90° C. for 24 hours. The mixture was allowed to cool, the excess of methanol was evaporated at vacuum, the residue was diluted with 1.5 l of water, 1.5 l of sodium bicarbonate saturated solution and 5 l of toluene and then stirred for 30 minutes. The insoluble material was filtered, washed twice with 1 l of toluene; the aqueous phase was extracted with 2 l of toluene, and the organic phases were filtered using a filter paper and washed with water. The toluene phase was concentrated at vacuum to give a blackish, viscous liquid residue weighing 1.391 kg (88%), which was distilled at vacuum to give 1.1 kg (70%) of colourless liquid at 124°-137° C./0.03-0.025 tors, nD20 =1.5533, IR and 1H-NMR spectra were consistent with structure.
Wird geladen…
