Phenol → HCID 18362102, Verbindung

HRID 1857829Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1857829
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[CH2:10]=[C:11]([CH:19](OC(=O)C)[C:20]([Cl:23])([Cl:22])[Cl:21])[C:12]([O:14][CH2:15][CH2:16][CH2:17][CH3:18])=[O:13].[O-]C1C=CC=CC=1>O1CCCC1.CCOCC.O>[CH2:10]=[C:11]([CH:19]([O:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[C:20]([Cl:21])([Cl:23])[Cl:22])[C:12]([O:14][CH2:15][CH2:16][CH2:17][CH3:18])=[O:13]

Komponenten

8

Edukt 4

HCID 996PhenolHCID 24758Sodium hydrideHCID 119047PhenolateHCID 11220844Butyl 2-methylene-3-acetoxy-4,4,4-trichlorobutyrate

Produkt 1

HCID 18362102HCID 18362102, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittel3×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Phenol (2.0 g) in 15 ml of tetrahydrofuran (THF) was slowly added to sodium hydride (1.0 g, 60% in oil) suspended in 5 ml THF at 0° C. Fifteen minutes later, 3.0 g of butyl 2-methylene-3-acetoxy-4,4,4-trichlorobutyrate (crude, GC: 86%) in 10 ml THF was slowly dropped into the phenoxide solution. The reaction was stirred at 0° C. for 3 hours and then permitted to warm to room temperature. The reaction was worked up by addition of 50 ml of water and 50 ml of ether. The organic layer was separated and the solvents were removed by vacuum. The resulting yellow oil was transferred to an alumina column and the product was eluted out with hexanes. A slightly yellow oil was obtained after removal of the hexanes, 3.1 g. The product was confirmed by NMR spectroscopy to be butyl 2-methylene-3-phenoxy-4,4,4-trichlorobutyrate.

Aufarbeitung

  1. temperatureto warm to room temperature
  2. customThe organic layer was separated
  3. customthe solvents were removed by vacuum
  4. washthe product was eluted out with hexanes
  5. customA slightly yellow oil was obtained
  6. customafter removal of the hexanes, 3.1 g

Quellen und Nachweise

ORD-Eintrag
ord-7d9e934bbe1348a693e14400cdbc15c7
Quelldatensatz
uspto-grants-2000_11
Patentnummer
US06147251

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