Acetone → Methyl 5-cyanopentanoate

HRID 1439537Notes

Reaction equation

HRID 1439537 reaction equation
[C:1](#[N:6])[CH2:2][CH2:3][CH:4]=[CH2:5].N1C=CC=CC=1.[CH3:13][OH:14].C[C:16](C)=[O:17]>[C]=O.[CH-]=O.[CH-]=O.[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[Co].[Co+2]>[CH3:13][O:14][C:16](=[O:17])[CH2:5][CH2:4][CH2:3][CH2:2][C:1]#[N:6]

Participants

7

Reactant 4

HCID 180AcetoneHCID 887MethanolHCID 1049PyridineHCID 116044-Pentenenitrile

Product 1

HCID 554130Methyl 5-cyanopentanoateYield 75.1%

Reagents, catalysts & solvents 2

HCID 25049Dicobalt Octacarbonyl (stabilized with 1-5% Hexane)CatalystHCID 178418416HCID 178418416, compoundSolvent2×

Conditions

Temperature
160 °C

Procedure

A mixture of 8.1 parts of 4-pentenonitrile, 1.4 parts of dicobalt octacarbonyl, 2.6 parts of pyridine, 8 parts of methanol and 30 parts of acetone is reacted in the same way as in Example 1. The pressure is brought to 200 bars by forcing in carbon monoxide at room temperature. The autoclave is heated to 160° C, the pressure is raised to 300 bars by forcing in further carbon monoxide, and the autoclave is shaken for two hours under these conditions. Fractional distillation of the material discharged from the autoclave gives 10.6 parts of 5-cyanovaleric acid methyl ester (75.1% of theory); boiling point 122°-124° C/11 mm Hg.

Workup

  1. customis reacted in the same way as in Example 1
  2. temperaturethe pressure is raised to 300 bars
  3. distillationFractional distillation of the material

Sources & evidence

ORD record
ord-f9c20d1089c1415ba4841aa3e5adb3f6
Source dataset
uspto-grants-1977_11
Patent number
US04060543

Reaction notes

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