2-Methylbenzenesulfonic acid → 1H-Indene, 2-bromo-
Reaction equation
[Br:1][C@@H:2]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C@H:3]1O.C1(C)C(S(O)(=O)=O)=CC=CC=1>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH2:10][C:9]2[C:4]([CH:3]=1)=[CH:5][CH:6]=[CH:7][CH:8]=2Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A 500 mL flask was charged with 25.5 g (120 mmol) of trans-2-bromo-1-indanol, 1 g of toluenesulfonic acid and 350 mL of toluene. This was capped with a Dean-Stark trap and heated to reflux for two hours at which time the system was cooled to room temperature and the volatiles removed in vacuo to leave a dark oil. The residue was taken up into hexanes and eluted through a silica pad using hexanes. Removal of the volatiles in vacuo gave 22.5 g (96 percent) of a light yellow oil.
Workup
- customThis was capped with a Dean-Stark trap
- temperatureheated
- temperatureto reflux for two hours at which time the system
- customthe volatiles removed in vacuo
- customto leave a dark oil
- washeluted through a silica pad
- customRemoval of the volatiles in vacuo
Sources & evidence
- ORD record
- ord-1c7e89d4d4514972a067ddc65a248326
- Source dataset
- uspto-grants-2006_08
- Patent number
- US07098356B2
Reaction notes
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