Ethanol, 2-chloro-, 1-(4-methylbenzenesulfonate) → HCID 20035829, compound

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Reaction Steps

In a 20-liter reactor provided with a mechanical stirrer and reflux cooler, 1078 g of methyl 2,3-dihydro-5-hydroxy-1H-inden-1-carboxylate were dissolved with 9 l of dry methyl ethyl ketone, 1162 g of anhydrous potassium carbonate were added and stirred for 30 minutes; then 1448 h of 2-chloroethyl p-toluensulphonate were added and refluxed in oil bath for 50 hours. The mixture was allowed to cool, the insoluble solid was filtered and washed twice with acetone over the same filter. The filtrate was evaporated and dried at vacuum, the residue was dissolved in 4.7 l of toluene and extracted with 1.8 l of 3N sodium hydroxyde solution through the decantation funnel and mechanical stirring for 15 minutes; then it was neutralized with water and dried. After evaporation of solvent at vacuum, the residue as reddish liquid weighed 1419 g (99%). Thin-layer chromatography (silica-gel) showed a major spot and a slight shadow at lower Rf. Cl analysis correct. It was used for the following synthesis step without further purification.

Provenance & Evidence