Water → Hexyl (R)-2-[4-(5-nonyl-1,3-dioxin-2-yl)phenoxy]propanoate

HRID 1164773ノート

反応式

HRID 1164773 の反応式
[OH:1][CH2:2][CH:3]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[CH2:4][OH:5].[C:15]1([CH3:25])[CH:20]=[CH:19][C:18](S(O)(=O)=O)=[CH:17][CH:16]=1.[OH2:26].CN(CC[C:32]([C:34]1[CH:39]=[CH:38][C:37]([N+]([O-])=O)=[CH:36]C=1)=[O:33])C>C1(C)C=CC=CC=1>[CH2:6]([C:3]1[CH2:2][O:1][CH:25]([C:15]2[CH:20]=[CH:19][C:18]([O:26][C@H:3]([CH3:4])[C:2]([O:33][CH2:32][CH2:34][CH2:39][CH2:38][CH2:37][CH3:36])=[O:1])=[CH:17][CH:16]=2)[O:5][CH:4]=1)[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]

参加物

6

反応物 4

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 1927564-Nitro-3-dimethylaminopropiophenoneHCID 39697442-Nonylpropane-1,3-diol

生成物 1

HCID 131716325Hexyl (R)-2-[4-(5-nonyl-1,3-dioxin-2-yl)phenoxy]propanoate収率 68%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒2 回

実験手順

A mixture of 2-hydroxymethyl-1-undecanol (10 mmole) HFPP (10 mmole) and p-toluenesulphonic acid (50 mg) in toluene (50 ml) was heated at reflux while allowing water to distil out. When reaction was complete the excess toluene was removed by distillation and the product allowed to cool before dilution with dichloromethane. After washing with saturated NaHCO3 solution the mixture was distilled to give a colourless liquid identified as NDPP by IR, 1H NMR and mass spectroscopy and elemental analysis (yield: 68%; bp: 230°-40° C. at 0.3 mbar; SOR: 5.9,c=3). The product was a 85:15 mixture of the trans and cis isomers.

後処理

  1. temperaturewas heated
  2. temperatureat reflux
  3. customto distil out
  4. customWhen reaction
  5. customwas removed by distillation
  6. temperatureto cool before dilution with dichloromethane
  7. washAfter washing with saturated NaHCO3 solution the mixture
  8. distillationwas distilled
  9. customto give a colourless liquid
  10. additiona 85:15 mixture of the trans and cis isomers

出典と根拠

ORDレコード
ord-a766fb33b03f4b87945c879441cc9c40
出典データセット
uspto-grants-1990_03
特許番号
US04906402

反応ノート

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