Diazomethane → HCID 54044568, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 4-pentyl-benzoic acid (1.178 g, 6.13 mmol) and oxalyl chloride (630 uL, 855 mg, 6.74 mmol, 1.1 eq) in dichloromethane (15 mL) was stirred at 22° C. for 10 min, then treated with one drop of N,N-dimethylformamide at 22° C. {Caution, gas evolution may become brisk}. After gas evolution was no longer observed, the flask was fitted with a condenser and warmed to reflux for 30 min. The solution was cooled to -5° C., and cannulated into a cold (-5° C.), ethereal solution of diazomethane (40 mL). After the solution was stirred at -5° C. for 30 min, the flask was removed from the cold bath and the yellow solution was allowed to stir at 22° C. for 2 hrs (preferably in the dark). The solution was concentrated in vacuo, and purified by flash chromatography (5% ethyl acetate in hexane) to provide 33 mg (1.3%) of 2-chloro-4'-(n-pentyl) acetophenone and 586 mg (44%) of 4'-(n-pentyl) diazoacetophenone as a bright yellow oil.

Provenance & Evidence