1-Butanol → N,N-Dimethylaniline

Participants

Reaction Conditions

Reaction Steps

Methyl squarate 0.64 grams, 5 millimoles, prepared as described in the Journal American Chemical Society, Vol. 88, pp. 1533-1536 (1966) was placed in a 100 milliliter 3-neck flask containing 0.1 milliliters of concentrated sulfuric acid, 1.23 grams, 10.2 millimoles of N,N-dimethylaniline, and 10 milliliters of dry 1-butanol (dried over 3 Angstrom molecular sieves). The above mixture was brought to reflux at an oil bath temperature of about 126° C. under a nitrogen atmosphere. After 24 hours, the mixture was cooled to room temperature, and 2 milliliters triethylanime, 30 milliliters ether/methanol (1:1) were added to the solution mixture. The precipitated product, bis(4-dimethylaminophenyl)squaraine was separated by filtration with a medium sintered glass funnel, followed by washing with an ether/methanol (1:1) solution, this washing continuing until the filtrate is light blue. After vacuum drying, there resulted 0.59 grams (37 percent), of bis(4-dimethylaminophenyl)squaraine as identified by a comparison of its properties, including melting point, and infrared (IR) spectrum with identical data generated for the squaraine obtained from the reaction of N,N-dimethylaniline and squaric acid.

Provenance & Evidence