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Monobenzone → Methyl 2-[(4-{3-[4-(benzyloxy)phenoxy]propyl}phenoxy)methyl]benzoate

HRID 2112017
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2112017
[OH:1][CH2:2][CH2:3][CH2:4][C:5]1[CH:22]=[CH:21][C:8]([O:9][CH2:10][C:11]2[CH:20]=[CH:19][CH:18]=[CH:17][C:12]=2[C:13]([O:15][CH3:16])=[O:14])=[CH:7][CH:6]=1.[CH2:23]([O:30][C:31]1[CH:36]=[CH:35][C:34](O)=[CH:33][CH:32]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(P(=CC#N)(CCCC)CCCC)CCC>C1(C)C=CC=CC=1>[CH2:23]([O:30][C:31]1[CH:36]=[CH:35][C:34]([O:1][CH2:2][CH2:3][CH2:4][C:5]2[CH:6]=[CH:7][C:8]([O:9][CH2:10][C:11]3[CH:20]=[CH:19][CH:18]=[CH:17][C:12]=3[C:13]([O:15][CH3:16])=[O:14])=[CH:21][CH:22]=2)=[CH:33][CH:32]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1
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Komponenten

5

Edukt 3

HCID 7638MonobenzoneHCID 4622928CyanomethylenetributylphosphoraneHCID 10780567Methyl 2-((4-(3-hydroxypropyl)phenoxy)methyl)benzoate

Produkt 1

HCID 68869717Methyl 2-[(4-{3-[4-(benzyloxy)phenoxy]propyl}phenoxy)methyl]benzoateAusbeute 64,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140Toluene
Lösungsmittel

Versuchsvorschrift

Methyl 2-{[4-(3-hydroxypropyl)phenoxy]methyl}benzoate (0.50 g, 1.66 mmol) and 4-(benzyloxy)phenol (0.33 g, 1.66 mmol) was added to a dry round bottomed flask fitted with a septum Dry toluene (10 ml) was added and N2 was flushed through the mixture for 5 minutes. (Tributylphosphoranylidene)acetonitrile (0.80 g, 3.33 mmol) was added dropwise and the reaction was performed in a single node microwave oven. After removing the solvent by evaporation the crude was purified by preparative HPLC (started with acetonitrile/buffer 60/40 and then the acetonitrile concentration was increased to 100%, the buffer was a mixture of acetonitrile/water 10/90 and ammonium acetate (0.1 M, column KR-100-7-C8, 50 mm×250 mm, flow 40 ml/min)). The product containing fractions were pooled and the acetonitrile was removed by evaporation. EtOAc (10 ml) was added and the organic phase was washed with two portions of brine and dried (MgSO4). Removing the solvent by evaporation gave 0.515 gram of methyl 2-[(4-{3-[4-(benzyloxy)phenoxy]-propyl}phenoxy)methyl]benzoate (yield 64.1%).

Aufarbeitung

  1. additionwas added
  2. customN2 was flushed through the mixture for 5 minutes
  3. customthe reaction was performed in a single node microwave oven
  4. customAfter removing the solvent
  5. customby evaporation the crude
  6. customwas purified by preparative HPLC (
  7. concentrationthe acetonitrile concentration
  8. temperaturewas increased to 100%
  9. additiona mixture of acetonitrile/water 10/90 and ammonium acetate (0.1 M, column KR-100-7-C8, 50 mm×250 mm, flow 40 ml/min))
  10. additionThe product containing fractions
  11. customthe acetonitrile was removed by evaporation
  12. additionEtOAc (10 ml) was added
  13. washthe organic phase was washed with two portions of brine
  14. dry with materialdried (MgSO4)
  15. customRemoving the solvent
  16. customby evaporation

Quellen und Nachweise

ORD-Eintrag
ord-368ce849ae60442aba721e0c86c78c50
Quelldatensatz
uspto-grants-2009_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07521461B2

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