temperature diluted with toluene 30 ml washed with ammonium chloride 2 u00d7 60 ml dried with magnesium sulfate and the solvent removed under reduced pressure a yield of 3 3 g 78 of product was obtained after trituration of the crude material with hexane mp 90 u00b0 93 u00b0 c to a slurry of 8 3 g 11 4 mmol in water 60 ml is added lithium hydroxide monohydrate 0 7 g 16 2 mmol and the mixture heated to 65 u00b0 c when no more starting material remains by tlc hex etoac 9 1 the mixture is cooled overnight the precipitated solids are filtered and then slurried in ethyl acetate 45 ml deionized water 25 ml is added to this slurry which is then acidified with 10 aqueous hydrochloric acid to a ph of 1 2 the layers are separated and the ethyl acetate phase concentrated to dryness to give 2 chloro cis 5a 8 9 9a tetrahydrodibenzofuran 4 carboxylic acid 9 as a white solid mp 147 u00b0 150 u00b0 c the acid 9 6 5 g 26 0 mmol is slurried in 200 ml of ethanol in a parr shaker reaction bottle 5 palladium on carbon 0 65 g is added to this and.