4-Diethylamino-2-methylbenzaldehyde synthesis

Yield: 82 g (429.3 mmol, 73%)

Reaction Conditions:

with trichlorophosphate in N,N-dimethyl-formamide

Steps:

S.1 Synthesis of 4-N,N-diethylamino-2-methylbenzaldehyde
Synthesis Example 1 Synthesis of 4-N,N-diethylamino-2-methylbenzaldehyde 45 g (586.6 mmol) of N,N-dimethylformamide and 91.9 g (586.6 mmol) of phosphorus oxychloride were placed in a 500 ml four-necked flask, and then a mechanical stirrer, a thermometer, a dropping funnel and a reflux condenser were set to the flask. Since heat generation begins upon mixing of the two reagents, the mixture was stirred well while cooling with water. Then, with the reaction system kept at a temperature below 30°C, 95.6 g (586.6 mmol) of N,N-diethyl-m-toluidine was added dropwise over a period of about one hour, after which stirring was further continued for 2 hours. The resulting reaction mixture was poured into ice-cold water and neutralized with 10 N sodium hydroxide. The organic matter was extracted with ether, and after drying the extract, the ether was distilled away. The residue was distilled under reduced pressure to obtain the objective compound. Yield: 82 g (429.3 mmol, 73%), boiling point: 175-181°C (at 4 mmHg).

References:

Hitachi Chemical Co., Ltd. EP465105, 1992, A2