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

HRID 1164773노트

반응식

HRID 1164773 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 1140Toluene용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-a766fb33b03f4b87945c879441cc9c40
출처 데이터셋
uspto-grants-1990_03
특허 번호
US04906402

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