Reaktion #8505

Reaktionsgleichung

sodium hydroxide

2-butene-1,4-diol

benzyl chloride

→

( 18 )

Ausbeute 114.5%

1,4-Dibenzyloxy-2-butene

Ausbeute 114.5%

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction mixture was cooled down
2. 2
   Sonstigeseparated
3. 3
   workup.ADDITIONafter the addition of water (90 ml)
4. 4
   workup.ADDITIONTo the organic layer was added sulfuric acidic brine
5. 5
   Sonstigeseparated
6. 6
   workup.ADDITIONmixed with ethyl acetate
7. 7
   Einengenconcentrated under reduced pressure

Vorschrift

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.

Quelle