Sulfuric acid magnesium salt (1:1) → 1-(4'-Fluorophenyl)-1,3-dihydroisobenzofuran-5-carbaldehyde
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:16]3[C:11](=[CH:12][C:13]([CH2:17][OH:18])=[CH:14][CH:15]=3)[CH2:10][O:9]2)=[CH:4][CH:3]=1.S([O-])([O-])(=O)=O.[Mg+2]>[O-2].[O-2].[Mn+4].C1(C)C=CC=CC=1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:16]3[C:11](=[CH:12][C:13]([CH:17]=[O:18])=[CH:14][CH:15]=3)[CH2:10][O:9]2)=[CH:4][CH:3]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 25 °C
Procedure
1-(4′-Fluorophenyl)-1,3-dihydroisobenzofuran-5-ylmethanol (60.5 kg) produced in Example 17 was added to toluene (520.9 kg) and manganese dioxide (544.8 kg, type HMH, manufactured by Toso) divided in three portions was added at 10-30° C. over 3 hr. The mixture was stirred at 23-27° C. for 1 hr, and the starting material was confirmed by HPLC to be 0.03%. Thereto were added Hyflo Super-Cel® (18.2 kg, Celite Co.) and anhydrous magnesium sulfate (30.2 kg). The mixture was cooled to about 10° C. over 2 hr and stirred at 2-10° C. for 40 min. The mixture was filtrated and the residue (waste manganese) was washed with toluene (284 kg). As a result of the analysis, 1-(4′-fluorophenyl)-1,3-dihydroisobenzofuran-5-carbaldehyde (60 kg, yield about 100%) was contained in the solution (917 kg). The crystals obtained by partial concentration of the solution showed the same physical properties as in Example 18.
Workup
- additionwas added at 10-30° C. over 3 hr
- temperatureThe mixture was cooled to about 10° C. over 2 hr
- stirringstirred at 2-10° C. for 40 min
- filtrationThe mixture was filtrated
- washthe residue (waste manganese) was washed with toluene (284 kg)
Sources & evidence
- ORD record
- ord-1dd78ab257e84d08beafb51f65b71c68
- Source dataset
- uspto-grants-2002_08
- Patent number
- US06433196B1
Reaction notes
Loading…