Water → 4-Formyl-2,2,6,6-tetramethylbenzo[1,2-d:4,5-d']bis(1,3)dioxole
Reaction equation
[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]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Procedure
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%).
Workup
- addition100 mmol) was added
- customto rise to 0° C
- customwas recooled to -20° C.
- extractionThe mixture was extracted with diethyl ether (3×300 mL)
- washthe combined organic phase was washed with water (2×100 mL)
- dry with materialdried (Na2SO4)
- customevaporated
- customdried
Sources & evidence
- ORD record
- ord-e881a7b2fd5d48879d93180014d900a0
- Source dataset
- uspto-grants-1997_02
- Patent number
- US05599522
Reaction notes
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