Water → 2,15-Hexadecanedione

HRID 1058151Notes

Reaction equation

HRID 1058151 reaction equation
[C:1]([CH:4]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH:19]([C:24](=[O:26])[CH3:25])C(OC)=O)C(OC)=O)(=[O:3])[CH3:2].[Cl-].[Na+].O>CS(C)=O>[CH3:2][C:1](=[O:3])[CH2:4][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:24](=[O:26])[CH3:25]

Participants

5

Reactant 3

HCID 962WaterHCID 5234Sodium ChlorideHCID 11451539HCID 11451539, compound

Product 1

HCID 4580962,15-Hexadecanedione

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

0.37 g (1 mmol) of dimethyl 2,13-bisacetyl-1,14-tetradecanedioate were dissolved in 20 ml of DMSO and refluxed with 0.06 g (0.1 mmol) of sodium chloride and 0.04 g (2 mmol) of water for 3 h at 155 to 160° C. For work-up, the DMSO is firstly distilled off under reduced pressure, and the residue is distilled using a bulb tube. This gives 0.21 g of hexadecane-1,15-dione. Accordingly, the yield of 1,15-hexadecanedione is 82%, based on 1,9-decadiene.

Workup

  1. distillationFor work-up, the DMSO is firstly distilled off under reduced pressure
  2. distillationthe residue is distilled

Sources & evidence

ORD record
ord-7776b98ac6fa4aff833f18a930f30b20
Source dataset
uspto-grants-2003_02
Patent number
US06515154B2

Reaction notes

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