Acetone → HCID 178436341, compound

Participants

Reaction Steps

A portion of the reaction product of a 1 to 2 mole ratio of 2,4,6-trimethyl pyridine and p-hydroxy benzaldehyde (7.30 grams, 0.0443 moles of hydroxyl groups) from 1-A above and acetone (150 grams) were added to a 1-liter glass resin kettle and maintained under a nitrogen atmosphere. Stirring and cooling were both started and when the temperature of the slurry reached 0° C., cyanogen bromide was added (4.93 grams, 0.0466 mole). After five minutes (300 s), triethylamine (4.51 grams, 0.0466 mole) was added dropwise over a four minute (240 s) period and so as to maintain the reaction temperature between 0° and 4° C. The reaction was allowed to progress for an additional 30 minutes (1800 s) between reaction temperatures of -1° to 5° C. After this time, the reaction slurry was filtered. The recovered filtrate was added to 750 milliliters of deionized water producing a voluminous pale white colored precipitate. The precipitate was recovered by filtration, washed with 100 milliliters of deionized water and then dried under vacuum at 25° C. to a constant weight of 2.2 grams. The unreacted trimethyl pyridine and p-hydroxy benzaldehyde adduct as well as triethylamine hydrochloride were recovered from the filter (5.2 grams), as a pale white colored powder. Infrared spectrophotometric analysis of a potassium bromide pellet of the product revealed the presence of cyanate group absorbance (2225 cm-1 and 2260 cm-1) accompanied by a substantial absence of a hydroxy group absorbance (3300 cm-1). As expected, trans-unsaturation absorbance (970 cm-1) and aromatic carbon-oxygen absorbance (1250 cm-1) remained.

Provenance & Evidence