Ethanol → HCID 54074187, compound

Participants

Reaction Steps

1.0 g (6.0 mmol) of 3-diethylamino-phenol is dissolved in 29 g of absolute ethanol with exclusion of moisture. 10 g of basic aluminium oxide are then allowed to trickle into the solution, with vigorous stirring. 0.7 g (6.0 mmol) of chloroacetyl chloride is added dropwise through an attached reflux condenser. The dark violet reaction mixture is heated to the boiling point under reflux, with vigorous stirring. After 2 hours, 1.0 ml (12 mmol) of chloroacetyl chloride is added dropwise through the reflux condenser. After a further 30 minutes, a further 1.5 ml (18 mmol) of chloroacetyl chloride and 2 g of basic aluminium oxide are added. After 10 minutes, the reaction mixture becomes dark red in colour. The reaction mixture is left to stand at 60-70° C. for 60 hours. Finally, the mixture is filtered with suction through a G4 frit and the solid is washed several times with absolute ethanol until the wash solution is virtually colourless. The dark red organic phases are combined. The ethanol is stripped off on a rotary evaporator. 3 g of a dark red, highly viscous residue are obtained, this being purified by column chromatography over silica gel using chloroform as the mobile phase. The colorant is isolated as a red-violet fraction in the first runnings. After the solvent has been stripped off, the resulting dark red solid is dried under an oil pump vacuum at 95° C. for 5 hours.

Provenance & Evidence