2-(2,4-Bis(1,1-dimethylpropyl)phenoxy)butyryl chloride → HCID 20313399, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 82 g of 2'-methoxy-5'-nitro-(2-ethylthio-2methylpropionyl)acetanilide obtained in Synthesis Example 3 and 800 ml of glacial acetic acid was heated to 90° C. To the mixture, 80 g of reduced iron was gradually added over a four minute period under a nitrogen atmosphere and with stirring. The reaction mixture was cooled to room temperature, and 24.1 g of sodium acetate and then 97 g of 2-(2,4-di-tert-amylphenoxy)butyryl chloride were added, and the mixture was stirred vigorously for 1 hour. The reaction mixture was filtered to remove the insoluble substances. The filtrate was poured into 1 liter of ethyl acetate, washed 4 times, each with 1 liter of a saturated aqueous sodium chloride solution, and then dried with sodium sulfate. After distilling off ethyl acetate, the residue was recrystallized from ethanol to obtain 110 g (yield 75%) of Coupler (13) having a melting point of 65° to 67° C.

Provenance & Evidence