Catechol → Catechol Formaldehyde

Participants

Reaction Conditions

Reaction Steps

Catechol (440.0 grams (4.0 moles) from James River Corp., Camas, Wash.) and 162 grams of 37% aqueous formaldehyde (2.0 moles) were placed into a one-liter, three-necked, round-bottomed flask equipped with a paddle stirrer, thermometer, water-cooled condenser and heating mantle. Deionized water (400 milliliters) was added to the flask and stirring was started. The mixture was heated to 50° C., 75° C., 85° C., and finally to reflux temperature (approximately 100° C.) over a 15 minute interval. Refluxing continued for two hours, then the solution was cooled to about 60° C. Oxalic acid (4 grams; 0.044 moles) was added, and the temperature was raised to reflux temperature over a 30 minute interval. Refluxing continued for an additional two hours. At the end of this time, 50 millimeters Hg vacuum was applied. The pressure was gradually lowered to less than or equal to 0.8 millimeters Hg vacuum, and the temperature of the mixture allowed to rise to between 150° C. and 160° C. The mixture was maintained at this temperature and vacuum for 30 minutes. The vacuum and heat were removed. The contents were poured into an aluminum pan and allowed to cool to room temperature. After cooling, a reddish solid formed which was broken into small pieces and stored in an air-tight container. The yield was approximately 450 grams. Fourier transform infrared spectroscopy revealed a characteristic phenol hydroxyl group at 3375 cm-1, and other characteristic bands at 1515, 1282, 1258 and 1190 cm-1.

Provenance & Evidence