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

HRID 1164773Notes

Reaction equation

HRID 1164773 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-a766fb33b03f4b87945c879441cc9c40
Source dataset
uspto-grants-1990_03
Patent number
US04906402

Reaction notes

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