Water → 7-Hydroxy-6-methyl-2,3-dihydro-1h-indene-4-carbaldehyde
Reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:8]2[CH2:7][CH2:6][CH2:5][C:4]=2[C:3]=1[OH:11].C1N2CN3CN(C2)CN1C3.O.FC(F)(F)[C:25](O)=[O:26]>>[OH:11][C:3]1[C:4]2[CH2:5][CH2:6][CH2:7][C:8]=2[C:9]([CH:25]=[O:26])=[CH:10][C:2]=1[CH3:1]Participants
5
Conditions
- Temperature
- 90 °C
Procedure
5-Methylindan-4-ol (4.50 g) and hexamethylenetetramine (4.26 g) were dissolved in trifluoroacetic acid (100 mL), and the mixture was stirred at 90° C. overnight. Water was added to the reaction mixture. After stirring for 30 min, the reaction mixture was extracted with ethyl acetate. The organic layer was washed with water, saturated sodium hydrogen carbonate and brine successively, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure to give the title compound (4.76 g).
Workup
- stirringAfter stirring for 30 min
- extractionthe reaction mixture was extracted with ethyl acetate
- washThe organic layer was washed with water, saturated sodium hydrogen carbonate and brine successively
- dry with materialdried over anhydrous magnesium sulfate
- customThe solvent was removed under reduced pressure
Sources & evidence
- ORD record
- ord-6dbb9fcf3015454fad00c860dd746426
- Source dataset
- uspto-grants-2007_06
- Patent number
- US07230031B2
Reaction notes
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