Hydrochloric Acid → HCID 19782199, compound

Participants

Reaction Conditions

Reaction Steps

9.8 g (5.5 mmol) of 5-hydroxy-indan-2-carboxylic acid are dissolved in 20 ml of nitrobenzene and 20 ml of carbon disulphide and 16.12 g (121 mmol) of aluminum trichloride are added in portions. 7.8 g (66 mmol) of dimethylacryloyl chloride in 20 ml of nitrobenzene are then added dropwise and the mixture is heated to 90° C. for 3 h. After cooling, 40 ml of concentrated hydrochloric acid and 40 g of ice are added and the mixture is shaken twice with 100 ml of CH2Cl2 each time. The combined CH2Cl2 phases are evaporated, the nitrobenzene is distilled off in a water jet vacuum and the residue is taken up in 100 ml of 10% strength NaOH solution. The NaOH phase is shaken twice with 100 ml of CH2Cl2 each time, then acidified using concentrated HCl solution with ice cooling and extracted 3 times using 100 ml of CH2Cl2 each time. After drying over Na2SO4, the solution is evaporated and the residue is flash chromatographed on silica gel (eluent: CH2Cl2 /acetone 10:1)

Provenance & Evidence