Pentyl nitrite → Amyl Acetate

HRID 1719405Notes

Reaction equation

HRID 1719405 reaction equation
[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][O:6]N=O.[CH2:9]=[C:10]=[O:11].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CN1CCCC1=O>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:10]([CH3:9])=[O:11]

Participants

5

Reactant 3

HCID 10026Pentyl nitriteHCID 10038KeteneHCID 11776Triphenylphosphine

Product 1

HCID 12348Amyl AcetateYield 25%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

The procedures of Example 14 were followed, except that 80 ml (536.9 mmoles) of n-amyl nitrite was used and that ketene was introduced at the rate of 11.3 ml/min (0.50 mmole/min). During the reaction, however, 15 ml, of a solution of triphenylphosphine (0.092 g, 0.375 mmole) and stannous chloride (0.072 g, 0.375 mmole) in N-methylpyrrolidone was added to the reaction system in 2.5 ml portions every 1 hour, and the reaction was effected at 90° C. for 6 hours. The gas chromatographic analysis revealed that di-n-amyl malonate (136.0 mmoles, 74.8%) and n-amyl acetate (45.4 mmoles, 25.0%) were obtained.

Workup

  1. customDuring the reaction

Sources & evidence

ORD record
ord-505f95de40c44c519476d902139f26a9
Source dataset
uspto-grants-1985_09
Patent number
US04539423

Reaction notes

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