Methanesulfonic Acid → 2-Methoxy-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-one
Reaction equation
O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.CS(O)(=O)=O.[CH3:20][O:21][C:22]1[CH:23]=[C:24]([CH2:28][CH2:29][C:30]2[CH:38]=[CH:37][CH:36]=[CH:35][C:31]=2[C:32]([OH:34])=O)[CH:25]=[CH:26][CH:27]=1>>[CH3:20][O:21][C:22]1[CH:27]=[CH:26][C:25]2[C:32](=[O:34])[C:31]3[CH:35]=[CH:36][CH:37]=[CH:38][C:30]=3[CH2:29][CH2:28][C:24]=2[CH:23]=1Participants
4
Conditions
- Temperature
- 80 °C
Procedure
To 5 g of phosphorous pentoxide was added 50 ml of methane sulphonic acid. The mixture was heated to 80° C. for 1 hour. The reaction mixture was brought down to 40° C. and 3 g (11.7 mmol) of 2 was added as solid. The mixture was heated at 40° C. for 1 hour and cooled down to room temperature. The reaction mixture was poured into 300 ml of ice/water and extracted with 200 ml of ethyl acetate. The organic layer was washed with 2×150 ml of water, 2×150 ml of saturated NaHCO3 and 100 ml of water. The resulting organic layer was dried (Na2SO4) and concentrated to give 2.6 g (11.7 mmol, 94%) of 3 as off-white powder.
Workup
- customwas brought down to 40° C.
- temperatureThe mixture was heated at 40° C. for 1 hour
- temperaturecooled down to room temperature
- extractionextracted with 200 ml of ethyl acetate
- washThe organic layer was washed with 2×150 ml of water, 2×150 ml of saturated NaHCO3 and 100 ml of water
- dry with materialThe resulting organic layer was dried (Na2SO4)
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-a9a0539891cb4dca890e4d99d4488437
- Source dataset
- uspto-grants-2002_04
- Patent number
- US06368814B1
Reaction notes
Loading…