Toluene → HCID 86682043, compound
Reaction equation
[OH:1][C:2]1[C:3]([C:11](=[O:13])[CH3:12])=[CH:4][C:5]2[O:9][CH2:8][O:7][C:6]=2[CH:10]=1.C1N2CN3CN(C2)CN1C3.C1(C)C=CC=CC=1.FC(F)(F)[C:33](O)=[O:34]>>[C:11]([C:3]1[C:2]([OH:1])=[C:10]([CH:33]=[O:34])[C:6]2[O:7][CH2:8][O:9][C:5]=2[CH:4]=1)(=[O:13])[CH3:12]Participants
Conditions
- Temperature
- 40 °C
Procedure
A solution of 1-(6-hydroxybenzo[d][1,3]dioxol-5-yl)ethanone (1.5 g, 8.3 mmol) in trifluoroacetic acid (15 mL) was added with hexamethylenetetramine (1.7 g, 13 mmol), and the mixture was stirred at 40° C. for 12 hours. The reaction mixture was added with toluene, and then the solvent was evaporated under reduced pressure. The residue was dissolved in ethyl acetate, and the solution was successively washed with water, saturated aqueous sodium hydrogencarbonate, and saturated brine. The organic layer was dried over anhydrous magnesium sulfate, the solvent was concentrated under reduced pressure, and the residue was subjected to silica gel column chromatography (eluted with chloroform/methanol (100:0→97:3)) to obtain 6-acetyl-5-hydroxybenzo[d][1,3]dioxole-4-carboxaldehyde (0.11 g, 6%).
Workup
- customthe solvent was evaporated under reduced pressure
- dissolutionThe residue was dissolved in ethyl acetate
- washthe solution was successively washed with water, saturated aqueous sodium hydrogencarbonate, and saturated brine
- dry with materialThe organic layer was dried over anhydrous magnesium sulfate
- concentrationthe solvent was concentrated under reduced pressure
- washthe residue was subjected to silica gel column chromatography (eluted with chloroform/methanol (100:0→97:3))
Sources & evidence
- ORD record
- ord-9647e6fd72d845158127a8283fe767d1
- Source dataset
- uspto-grants-2015_10
- Patent number
- US09156827B2
Reaction notes
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