Ammonia → Cyclohexanone, trimethyl-

HRID 371964

反応式

HRID 371964 の反応式
[CH3:1][C:2]1([CH3:10])[CH2:7][CH2:6][CH2:5][CH:4](C)[C:3]1=[O:9].Cl[CH2:12]C=CCCl.N.O>C1COCC1>[CH3:12][CH:7]1[CH2:6][CH2:5][CH2:4][C:3](=[O:9])[C:2]1([CH3:1])[CH3:10]

参加物

6

反応物 4

HCID 222AmmoniaHCID 962WaterHCID 151221,4-Dichloro-2-buteneHCID 170002,2,6-Trimethylcyclohexanone

生成物 1

HCID 3016570Cyclohexanone, trimethyl-収率 19.6%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

28 g of 2,2,6-trimethyl-cyclohexanone are added dropwise to a suspension of Na vinylacetylide (prepared from 25 g of 1,4-dichlorobut-2-ene and 15 g of Na in liquid ammonia) in 200 ml of THF, whilst cooling, and the reaction mixture is stirred overnight at room temperature. 50 ml of water are then added, the aqueous phase is extracted with ether and the resulting organic phase is dried and concentrated. Subsequent fractional distillation gives 5.5 g of unconverted trimethylcyclohexanone and 20.7 g (corresponding to 68% of theory, based on ketone converted) of 2,2,6-trimethyl-1-(but-1'-yn-3'-en-1'-yl)-cyclohexanol of boiling point 62°-63° C/0.3 mm Hg and refractive index nD25 = 1.4982. Fragrance note: fresh, tart-woody, coniferous.

後処理

  1. temperaturewhilst cooling
  2. extractionthe aqueous phase is extracted with ether
  3. customthe resulting organic phase is dried
  4. concentrationconcentrated
  5. distillationSubsequent fractional distillation

出典と根拠

ORDレコード
ord-9a4f5dd4dae64917b167c5c127b60dfe
出典データセット
uspto-grants-1978_05
特許番号
US04088681

関連ノート

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