Catechol → 3-Nonylbenzene-1,2-diol

Participants

Reaction Conditions

Reaction Steps

Into a 500ml, 3-neck reaction vessel was placed 64.8g (0.3125 moles) of catechol, after which time it was heated to 104° C. under a nitrogen flow. After the catechol was completely melted, 3.25g (5% based on the wt. of the catechol) of borontrifluoride-etherate was added dropwise, with stirring. After adding all of the catalyst, 63.2g (0.25 moles) of 1-nonene was added, dropwise to the reaction mixture, the rate of addition being adjusted so as to maintain a temperature of 130° C. After all of the 1-nonene was added, the resultant mixture was allowed to react for 3 hours, after which time 100ml of a 10% sodium chloride solution was added to the reaction mixture. The resultant mixture was then stirred for 15 minutes at 95° to 100° C., after which time the bottom layer was separated. The mixture was again stirred at 95° to 100° C. for 15 minutes, after which time the bottom layer was again separated. The organic layer was then isolated to obtain a viscous, brown oil of the formula ##STR6##

Provenance & Evidence