Sodium Hydroxide → Z-4-[4-(2-benzyloxyethoxy)-phenyl]-3,4-diphenyl-but-3-en-1-ol

HRID 1289918Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1289918
[OH-].[Na+].[OH:3][CH2:4][CH2:5]/[C:6](/[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[C:7](/[C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=1)\[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[CH2:27]([O:34][CH2:35][CH2:36]Br)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[CH2:27]([O:34][CH2:35][CH2:36][O:20][C:17]1[CH:16]=[CH:15][C:14](/[C:7](/[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[C:6](\[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)/[CH2:5][CH2:4][OH:3])=[CH:19][CH:18]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Komponenten

6

Edukt 3

HCID 14798Sodium HydroxideHCID 73833Benzene, ((2-bromoethoxy)methyl)-HCID 13298065Z-4-(4-hydroxy-1,2-diphenyl-but-1-enyl)-phenol

Produkt 1

HCID 70117020Z-4-[4-(2-benzyloxyethoxy)-phenyl]-3,4-diphenyl-but-3-en-1-ol

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 74236Tetrabutylammonium BromideKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

The reaction vessel was charged with toluene (790 ml), 48% aqueous sodium hydroxide (790 ml), tetrabutylammonium bromide (2.12 g, 6.6 mmol) and Z-4-(4-hydroxy-1,2-diphenyl-but-1-enyl)-phenol (50 g, 0.16 mol) prepared by the method described by U.S. Pat. No. 4,996,225. The mixture was refluxed for 30 minutes. Benzyl-(2-bromoethyl)ether (Grobelny D. et al., Tetrahedron Letters 28, 2639-42, 1979) (41.7 g, 0.19 mol) was added to the reaction mixture and the refluxing was continued for 2 hours. Then the mixture was cooled to room temperature, layers were separated and aqueous phase was washed with toluene. Toluene phases were combined, washed with water, dried and evaporated to dryness. The residue was used in the next stage without further purification.

Aufarbeitung

  1. customprepared by the method
  2. temperatureThe mixture was refluxed for 30 minutes
  3. customlayers were separated
  4. washaqueous phase was washed with toluene
  5. washwashed with water
  6. customdried
  7. customevaporated to dryness
  8. customThe residue was used in the next stage without further purification

Quellen und Nachweise

ORD-Eintrag
ord-9991cd9a0675453885aea09e6a8bf636
Quelldatensatz
uspto-grants-1998_05
Patentnummer
US05750576

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