Sodium Hydroxide → 2-Phenyl-4-pentyn-2-ol

HRID 256733Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 256733
Cl[C:2]([CH2:4][C:5]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([OH:7])[CH3:6])=[CH2:3].[OH-].[Na+]>C1(C)C=CC=CC=1.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[C:8]1([C:5]([OH:7])([CH3:6])[CH2:4][C:2]#[CH:3])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Komponenten

5

Edukt 2

HCID 14798Sodium HydroxideHCID 22404520HCID 22404520, Verbindung

Produkt 1

HCID 5693552-Phenyl-4-pentyn-2-ol

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 74236Tetrabutylammonium BromideKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

20.00 Grams of the 2-chloro-4-phenyl-1-penten-4-ol were dissolved in 50 g of toluene, and 30.5 g of a 40% sodium hydroxide aqueous solution and 65.57 g of tetra-n-butylammonium bromide were added. The mixture was allowed to react at 50° C. for 30 hours, and then was subjected to separation. The organic phase was washed with water, and the toluene was distilled off under reduced pressure. The resultant oily substance was purified by silica gel column chromatography to give 11.37 g of 4-phenyl-1-pentyn-4-ol; nD21 =1.537 FI-MS m/e 160(M+) (Propargyl compound/allene compound 100.0/0.0).

Aufarbeitung

  1. customto react at 50° C. for 30 hours
  2. customwas subjected to separation
  3. washThe organic phase was washed with water
  4. distillationthe toluene was distilled off under reduced pressure
  5. customThe resultant oily substance was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-b598667bd9bc4ab2bf7104f9ce6af5b3
Quelldatensatz
uspto-grants-1993_11
Patentnummer
US05258529

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