Benzyl Chloride → 1,4-Bis(benzyloxy)-2-butene

HRID 8409

Reaktionsgleichung

Reaktionsgleichung von HRID 8409
[OH-].[Na+].[CH2:3]([OH:8])[CH:4]=[CH:5][CH2:6][OH:7].[CH2:9](Cl)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:9]([O:7][CH2:6][CH:5]=[CH:4][CH2:3][O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Komponenten

5

Edukt 3

HCID 7503Benzyl ChlorideHCID 80652-Butene-1,4-diolHCID 14798Sodium Hydroxide

Produkt 1

HCID 40541091,4-Bis(benzyloxy)-2-buteneAusbeute 114,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 74236Tetrabutylammonium BromideKatalysator

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To 48% aqueous sodium hydroxide (127.8 g) was added tetra-n-butylammonium bromide (3.3 g, 10 mmol). The mixture was heated to 60° C. To the mixture was added 2-butene-1,4-diol (17) (30.0 g, 340 mmol), to which was added dropwise benzyl chloride (94.8 g, 743 mmol) at 80±15° C. The mixture was stirred at the same temperature for 2 hours. The reaction mixture was cooled down, and separated after the addition of water (90 ml). To the organic layer was added sulfuric acidic brine. The solution was neutralized by aqueous sodium hydrogen carbonate, separated, mixed with ethyl acetate and concentrated under reduced pressure to yield the objective (18) (104.5 g, quantitative) as an oil residue.

Aufarbeitung

  1. temperatureThe reaction mixture was cooled down
  2. customseparated
  3. additionafter the addition of water (90 ml)
  4. additionTo the organic layer was added sulfuric acidic brine
  5. customseparated
  6. additionmixed with ethyl acetate
  7. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-4caad36be5ac4269aa3917d91c05067e
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07087764B2

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