Ethanol → 2,5-nonanedione

HRID 258947Notes

Reaction equation

HRID 258947 reaction equation
[CH3:1][CH2:2][CH2:3][CH2:4][CH:5]=[O:6].[CH:7]([C:9]([CH3:11])=O)=[CH2:8].C(N(CC)CC)C.C([OH:21])C>>[CH3:1][C:2](=[O:21])[CH2:3][CH2:4][C:5](=[O:6])[CH2:8][CH2:7][CH2:9][CH3:11]

Participants

5

Reactant 4

HCID 702EthanolHCID 6570Methyl vinyl ketoneHCID 8063PentanalHCID 8471Triethylamine

Product 1

HCID 111265032,5-nonanedione

Procedure

Following the procedure described in Example 1, 13.5 g (0.05 mol) of Cat. 1, 43.1 g (0.5 mol) of n-valeraldehyde, 35.1 g (0.5 mol) of methyl vinyl ketone, 500 ml of ethanol and 20.2 g (0.2 mol) of triethylamine are heated for 12 hours under nitrogen at the reflux temperature. For working up, the solvent is distilled, the cooled residue is taken up in chloroform, the chloroform phase is washed with dilute sulphuric acid and subsequently with water, the chloroform is removed and the liquid residue is distilled in a waterpump vacuum. Nonane-2,5-dione is obtained.

Workup

  1. distillationthe solvent is distilled
  2. washthe chloroform phase is washed with dilute sulphuric acid and subsequently with water
  3. customthe chloroform is removed
  4. distillationthe liquid residue is distilled in a waterpump vacuum

Sources & evidence

ORD record
ord-03063fefccd84353b39346574fd8c449
Source dataset
uspto-grants-1977_07
Patent number
US04035395

Reaction notes

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