Hydrochloric Acid → 9H-Fluoren-1-ol

Participants

Reaction Conditions

Reaction Steps

35.5g (0.1 mole) of 2-nitro-2'-hydroxy-5-t-octylazobenzene are added to the mixture of 60 ml of methanol, 2.3 g of fluorenone and 64 g of 50% aqueous solution of sodium hydroxide. The mixture is stirred at 70°-75° C. and to the mixture is slowly added 55.4 g (0.3 mol) of glucose in 55 ml of water over 2 hours. The reaction mixture is heated for an additional three hours, then 160 ml of methanol is added at 55°-60° C. and 14.2 g of 35% hydrochloric acid slowly added and stirred at 40°-50° C. for 20 minutes. During this time crystals should appear. Then more hydrochloric acid is added to attain pH 4-5. The reaction is cooled to 25° C. to yield 26.5 g (82%). Compared to Example 1, above, more than three times the amount of fluorenone is needed, more than double the reaction time is required, and a lower yield is obtained than when fluorenol is used.

Provenance & Evidence