Sodium Chloride → Methyl 3-oxo-7,11-dimethyl-dodeca-6,10-dienoate

HRID 2400158ノート

反応式

HRID 2400158 の反応式
[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]

参加物

7

反応物 5

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

生成物 1

HCID 53708905Methyl 3-oxo-7,11-dimethyl-dodeca-6,10-dienoate

試薬・触媒・溶媒 1

HCID 21877177toluene N-methylpyrrolidone溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-fe80c16b71244bbe8c598eaaf4a7b2b5
出典データセット
uspto-grants-1995_09
特許番号
US05453525

反応ノート

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