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

HRID 400293Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 400293
[CH3:1][C:2]1([CH3:16])[O:6][C:5]2[CH:7]=[C:8]3[O:12][C:11]([CH3:14])([CH3:13])[O:10][C:9]3=[CH:15][C:4]=2[O:3]1.C([Li])CCC.CN([CH:25]=[O:26])C.O>C1COCC1.C1(C)C=CC=CC=1.CC(O)=O>[CH:25]([C:15]1[C:4]2[O:3][C:2]([CH3:16])([CH3:1])[O:6][C:5]=2[CH:7]=[C:8]2[O:12][C:11]([CH3:14])([CH3:13])[O:10][C:9]=12)=[O:26]

Komponenten

8

Edukt 4

HCID 962WaterHCID 6228DimethylformamideHCID 109220852,2,6,6-Tetramethylbenzo[1,2-d:4,5-d']bis([1,3]dioxole)HCID 178418339Butyllithium

Produkt 1

HCID 189430854-Formyl-2,2,6,6-tetramethylbenzo[1,2-d:4,5-d']bis(1,3)dioxole

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 176Acetic AcidLösungsmittelHCID 1140TolueneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

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%).

Aufarbeitung

  1. addition100 mmol) was added
  2. customto rise to 0° C
  3. customwas recooled to -20° C.
  4. extractionThe mixture was extracted with diethyl ether (3×300 mL)
  5. washthe combined organic phase was washed with water (2×100 mL)
  6. dry with materialdried (Na2SO4)
  7. customevaporated
  8. customdried

Quellen und Nachweise

ORD-Eintrag
ord-dd7f0da26e6c47c7aa9717727054899d
Quelldatensatz
uspto-grants-1998_10
Patentnummer
US05827501

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