Pentyl nitrite → Amyl Acetate

HRID 1719402Notes

Reaction equation

[CH2:1]=[C:2]=[O:3].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:23][CH2:24][CH2:25][CH2:26][CH2:27][O:28]N=O>>[CH3:23][CH2:24][CH2:25][CH2:26][CH2:27][O:28][C:2]([CH3:1])=[O:3]

Participants

Reactant 3

HCID 10026Pentyl nitrite

HCID 10038Ketene

HCID 11776Triphenylphosphine

Product 1

HCID 12348Amyl AcetateYield 12.8%

Procedure

The procedures of Example 11 were followed, except that ketene was introduced at the rate of 32.0 ml/min (1.43 mmole/min) and that triphenylphosphine (0.066 g, 0.25 mmole) was dissolved in the further added n-amyl nitrite (50 ml). The reaction proceeded smoothly for three hours, during which no deactivation of the catalyst was observed. The reaction product was analyzed by gas chromatography, revealing that n-di-amyl malonate (165.6 mmoles, 64.5%) and n-amyl acetate (32.9 mmoles, 12.8%) were obtained.

Workup

additionwas introduced at the rate of 32.0 ml/min (1.43 mmole/min)

Sources & evidence

ORD record: ord-671fec72dd4e4503ac4eb288834dc9c9
Source dataset: uspto-grants-1985_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04539423

Reaction notes

Loading…