Trisodium citrate → HCID 54074187, compound

Participants

Reaction Steps

10.0 g (60.5 mmol) of 3-diethylaminophenol are mixed with 12.5 g (90.1 mmol) of bromoacetic acid at a reaction temperature of 60° C., with exclusion of moisture and vigorous stirring with a precision glass stirrer. 7.0 g (46 mmol) of phosphoryl chloride, 6.3 g (46 mmol) of phosphorus trichloride and 24.6 g (152 mmol) of anhydrous iron trichloride are added. After a reaction time of 24 hours, 3 parts of ice are added to the dark violet mixture and the solid mixture is dissolved with cautious heating and stirring. After addition of sodium citrate (as a complexing agent for Fe3+ -ions), the mixture is extracted by shaking three times with 80 ml of chloroform each time. The dark red organic phase is dried over MgSO4. After the solvent has been stripped off on a rotary evaporator, 55.66 g of dark violet, highly viscous crude product are obtained. 0.7 g of crude product are worked up by column chromatography over silica gel using chloroform as the mobile phase. The trans colorant isomer can be separated off as a red-violet fraction in the first runnings. After the solvent has been stripped off on a rotary evaporator, the resulting dark red solid is dried under an oil pump vacuum at 95° C. for 7 hours.

Provenance & Evidence