Pentyl nitrite → Amyl Acetate
Reaction equation
[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][O:6]N=O.[CH2:9]=[C:10]=[O:11].[C]=O>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.ClC1C=CC=CC=1>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:10]([CH3:9])=[O:11]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
To the same reaction vessel as in Example 9 were charged bistriphenylphosphinedibromopalladium (0.396 g, 0.5 mmole), stannous chloride (0.190 g, 1 mmole), tetra-n-butylammonium chloride (0.278 g, 1 mmole) and n-amyl nitrite (25 ml, 171.0 mmole), together with monochlorobenzene (200 ml). Then, ketene, carbon monooxide and nitrogen were introduced to the mixture at the rate of 26.4 ml/min (1.18 mmole/min), 300 ml/min and 100 ml/min, respectively, and the reaction was performed at 90° C. for 3 hours. During the reaction, a further n-amyl nitrite (50 ml, 342.0 mmoles) was added dropwise to the reaction mixture over 2.5 hours. The reaction mixture was analyzed by gas chromatography, revealing that di-n-amyl malonate (125.6 mmoles, 59.1%) and n-amyl acetate (24.7 mmoles) were obtained.
Workup
- customDuring the reaction
Sources & evidence
- ORD record
- ord-f06e48e88fd64a64b4bdbff37e4c7eb4
- Source dataset
- uspto-grants-1985_09
- Patent number
- US04539423
Reaction notes
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