Sodium Chloride → HCID 53708905, compound

HRID 2400158Notes

Reaction equation

HRID 2400158 reaction equation
[H-].[Na+].[CH2:3]([CH2:13][C:14](=[O:16])[CH3:15])/[CH:4]=[C:5](/[CH2:7][CH2:8][CH:9]=[C:10]([CH3:12])[CH3:11])\[CH3:6].[NH4+].[Cl-].[Na+].[Cl-].[CH3:21][O:22][C:23](=O)[O:24]C>C1(C)C=CC=CC=1.CN1CCCC1=O>[O:16]=[C:14]([CH2:13][CH2:3][CH:4]=[C:5]([CH3:6])[CH2:7][CH2:8][CH:9]=[C:10]([CH3:11])[CH3:12])[CH2:15][C:23]([O:22][CH3:21])=[O:24]

Participants

7

Reactant 5

HCID 5234Sodium ChlorideHCID 12021Dimethyl Carbonate2×HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 1549778Geranylacetone

Product 1

HCID 53708905HCID 53708905, compound

Reagents, catalysts & solvents 1

HCID 21877177toluene N-methylpyrrolidoneSolvent

Procedure

24 g (0.55M) of sodium hydride (55% dispersion in mineral oil) were added at 20° under nitrogen to a solution of 135 g (1.5M) of dimethylcarbonate in 500 ml of a mixture of toluene/N-methylpyrrolidone (9:1). The obtained mixture was heated to reflux (bath temperature 100°) then, during 1 h, there was added a solution of 0.5M of geranylacetone in 135 g (1.5M) of dimethylcarbonate, where upon the resulting reaction mixture was kept refluxing during 10 min. It was finally poured into a 10% aqueous solution of NH4Cl saturated with NaCl. An ether extraction, followed by the usual work up of the combined organic extracts and fractional distillation gave methyl 3-oxo-7,11-dimethyl-dodeca-6,10-dienoate.

Workup

  1. temperatureThe obtained mixture was heated
  2. temperatureto reflux (bath temperature 100°)
  3. customupon the resulting reaction mixture
  4. temperaturewas kept refluxing during 10 min
  5. extractionAn ether extraction
  6. distillationfollowed by the usual work up of the combined organic extracts and fractional distillation

Sources & evidence

ORD record
ord-fe80c16b71244bbe8c598eaaf4a7b2b5
Source dataset
uspto-grants-1995_09
Patent number
US05453525

Reaction notes

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