p-Toluenesulfonic acid monohydrate → 4-(2,6,6-Trimethylcyclohex-2-en-1-ylidene)but-2-en-2-yl acetate

HRID 616063ノート

反応式

HRID 616063 の反応式
[CH3:1][C:2]1[CH2:7][CH2:6][CH2:5][C:4]([CH3:9])([CH3:8])[C:3]=1/[CH:10]=[CH:11]/[C:12]([CH3:14])=[O:13].[OH2:15].[C:16]1([CH3:26])C=CC(S(O)(=O)=O)=CC=1>C(OC(C)=C)(=O)C>[CH3:1][C:2]1[C:3](=[CH:10][CH:11]=[C:12]([O:13][C:16](=[O:15])[CH3:26])[CH3:14])[C:4]([CH3:8])([CH3:9])[CH2:5][CH2:6][CH:7]=1

参加物

4

反応物 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 638014I2-Ionone

生成物 1

HCID 534067734-(2,6,6-Trimethylcyclohex-2-en-1-ylidene)but-2-en-2-yl acetate収率 14,611.2%

試薬・触媒・溶媒 1

HCID 7916Isopropenyl acetate溶媒

実験手順

96 g of β-ionone are dissolved in 500 ml of isopropenyl acetate and treated with 0.6 g of p-toluenesulphonic acid monohydrate. The mixture is stirred at reflux temperature under an inert gas atmosphere for 24 hours. The excess isopropenyl acetate is distilled off from the mixture under a vacuum (temperature ≤50°) and then the mixture is treated several times with hexane in order to liberate residual amounts of isopropenyl acetate and concentrated again. In this manner, there are obtained 108 g of brown-red 4-(2,6,6-trimethyl-2-cyclohexen-1-ylidene)-2-acetoxy-but-2-ene (formula II; R = acetyl).

後処理

  1. temperatureat reflux temperature under an inert gas atmosphere for 24 hours
  2. distillationThe excess isopropenyl acetate is distilled off from the mixture under a vacuum (temperature ≤50°)
  3. additionthe mixture is treated several times with hexane in order
  4. concentrationconcentrated again

出典と根拠

ORDレコード
ord-bbb70a5d73584764a415d632bd87e2a9
出典データセット
uspto-grants-1978_02
特許番号
US04072719

反応ノート

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