Hydrochloric Acid → 3,3-Dimethylspiro-(cyclopropane-1,1'-indene)-2-carboxylic acid 3-phenoxy-4-fluoro-benzyl ester

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Reaction Steps

5.05 g (0.0232 mol) of 3-phenoxy-4-fluoro-benzyl alcohol and 5.4 g (0.0232 mol) of 3,3-dimethyl-spiro(cyclopropane-1,1'-indene)-2-carboxylic acid chloride were dissolved in 100 ml of anhydrous toluene, and 2.5 g of pyridine, dissolved in 50 ml of toluene, were added dropwise at 20°-25° C., while stirring. The mixture was stirred at 25°-35° C. for a further 3 hours. The reaction mixture was poured into 150 ml of water, to which 5 ml of concentrated hydrochloric acid were added, and the organic phase was separated off and washed again with 100 ml of water. The toluene phase was then dried over sodium sulphate and the solvent was distilled off under a waterpump vacuum. Last residues of solvent were removed by brief incipient distillation at a bath temperature of 60° C./1 mm Hg. 8.3 g (86.4% of theory) of 3,3-dimethylspiro-(cyclopropane-1,1'-indene)-2-carboxylic acid 3-phenoxy-4-fluoro-benzyl ester were obtained as a viscous oil. The structure was confirmed by the 1H-NMR spectrum.

Provenance & Evidence