Reaktion #415367

Reaktionsgleichung

prenol

3-methyl-but-2-en-1-ol

1,1-dimethoxy-3-methyl-2-butene

prenol

3-methyl-but-2-en-1-ol

2,4-dinitrophenol

→

1-methoxy-1-(3-methylbut-2-enoxy)-3-methyl-2-butene

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeone-neck flask was placed
2. 2
   SonstigeThe resulting solution was degassed with nitrogen
3. 3
   Sonstigesealed with a serum
4. 4
   Sonstigecap
5. 5
   workup.ADDITIONThe reaction solution was then diluted with 100 ml
6. 6
   Waschenof hexane and washed with 3 × 100 ml
7. 7
   Extraktionwith extracted 1 × 50 ml
8. 8
   TrocknenThe combined hexane solutions were dried (Na2SO4)
9. 9
   Einengenconcentrated
10. 10
    Sonstigeto give 9.0 g
11. 11
    workup.DISTILLATIONDistillation of 8.3 g
12. 12
    Sonstigeat 20 mmHg and a bath temperature of 55°-60° gave 1.48 g
13. 13
    workup.DISTILLATIONContinued distillation initially at 0.20 mmHg
14. 14
    Sonstigegave 2.43 g

Vorschrift

In a 50 ml. one-neck flask was placed 5.5 g. (0.0422 mol.) of 1,1-dimethoxy-3-methyl-2-butene and 10.0 g. (0.116 mol.) of prenol and 0.40 g. (0.002 mol.) of 2,4-dinitrophenol. The resulting solution was degassed with nitrogen and sealed with a serum cap and stirred at room temperature for 76 hours. The reaction solution was then diluted with 100 ml. of hexane and washed with 3 × 100 ml. of 1.0 N aqueous NaOH solution and 2 × 100 ml. of saturated aqueous NaCl solution. The combined water washings were back with extracted 1 × 50 ml. of hexane. The combined hexane solutions were dried (Na2SO4) and concentrated to give 9.0 g. of crude product. Distillation of 8.3 g. at 20 mmHg and a bath temperature of 55°-60° gave 1.48 g. of prenol. Continued distillation initially at 0.20 mmHg gave 2.43 g. of 1-methoxy-1-(3-methylbut-2-enoxy)-3-methyl-2-butene (b.p. 40°-45° at 0.20 mmHg) and finally at 0.050 mmHg gave 3.29 g. of 1,1-bis-(3-methylbut-2-enoxy)-3-methylbut-2-ene (b.p. 70°-75° at 0.050 mmHg).

Quelle