Reaktion #1537230

Reaktionsgleichung

Water

2,2,6,6-Tetramethylbenzo[1,2-d:4,5-d']bis(1,3)-dioxole

2,2,6,6-Tetramethylbenzo[1,2-d:4,5-d']bis(1,3)dioxole

n-Butyl lithium

DMF

→

title compound

4-Formyl-2,2,6,6-tetramethylbenzo[1,2-d:4,5-d']bis(1,3)-dioxole

Lösungsmittel

AcOH

THF

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITION100 mmol) was added
2. 2
   Sonstigeto rise to 0° C
3. 3
   Sonstigewas recooled to -20° C.
4. 4
   ExtraktionThe mixture was extracted with diethyl ether (3×300 mL)
5. 5
   Waschenthe combined organic phase was washed with water (2×100 mL)
6. 6
   Trocknendried (Na2SO4)
7. 7
   Sonstigeevaporated
8. 8
   Sonstigedried

Vorschrift

2,2,6,6-Tetramethylbenzo[1,2-d:4,5-d']bis(1,3)-dioxole (20.0 g, 90 mmol (Example 5)) was dissolved in THF (300 mL) and cooled to -20° C. n-Butyl lithium (38.0 mL), 2.5M in toluene, 100 mmol) was added and the temperature was allowed to rise to 0° C. The mixture was recooled to -20° C. and DMF (6.9 mL, 90.0 mmol) was added. The reaction mixture was stirred over night while allowing the temperature to increase to room temperature. Water (200 mL) and AcOH (5 mL) was added. The color changed from light yellow to strong orange. The mixture was extracted with diethyl ether (3×300 mL) and the combined organic phase was washed with water (2×100 mL), dried (Na2SO4) and evaporated. The product was trituated twice with petroleum ether and dried, yielding the pure title compound; 16.3 g (72%).

Quelle