Pentyl nitrite → Amyl Acetate

Participants

Reaction Steps

To the same reaction vessel as in Example 9 were charged bistriphenylphosphinedibromopalladium (0.198 g, 0.25 mmole), stannous chloride (0.095 g, 0.5 mmole), tetra-n-butylammonium chloride (0.139 g, 0.5 mmole) and n-amyl nitrite (60 ml, 406.6 mmoles), together with monochlorobenzene (200 ml). Then, ketene, carbon monooxide and nitrogen were introduced to the mixture at the rate of 10.4 ml/min (0.46 mmole/min), 300 ml/min and 100 ml/min, respectively, and the reaction was effected for 5 hours. During the reaction, 10 ml of a solution of triphenylphosphine and stannous chloride (0.25 mmole each) in N-methylpyrrolidone was added to the reaction system in 2.5 ml portions every 1 hour. The reaction proceeded smoothly for 5 hours without termination of the reaction to give di-n-amyl malonate (116.2 mmoles, 83.8%) and n-amyl acetate (20.5 mmoles, 14.7%).

Provenance & Evidence