Methanol → Methyl 2-(2-iodophenyl)acetate
Reaction equation
[I:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([OH:11])=[O:10].OS(O)(=O)=O.[CH3:17]O>>[I:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([O:11][CH3:17])=[O:10]Participants
4
Conditions
- Temperature
- 80 °C
Procedure
To a solution of 2-(2-iodophenyl)acetic acid (5.00 g, 19.1 mmol) in MeOH (150 mL) was added concentrated aqueous H2SO4 (250 μL) and the resulting mixture was stirred at 80° C. under nitrogen for 16 hours. The volatiles were removed by evaporation under reduced pressure and the residue was taken up in EtOAc (100 mL). The resulting solution was washed with 10% aqueous NaHCO3 (100 mL), dried (MgSO4) and the volatiles evaporated under reduced pressure to give the title compound I1 as a clear liquid (5.20 g, 99%); 1H NMR (400 MHz, CDCl3) δ 7.85 (dd, J=7.9, 1.0 Hz, 1H), 7.35-7.27 (m, 2H), 6.97 (m, 1H), 3.81 (s, 2H), 3.72 (s, 3H).
Workup
- customThe volatiles were removed by evaporation under reduced pressure
- washThe resulting solution was washed with 10% aqueous NaHCO3 (100 mL)
- dry with materialdried (MgSO4)
- customthe volatiles evaporated under reduced pressure
Sources & evidence
- ORD record
- ord-a38cff65f7f849f8932c20448e52d351
- Source dataset
- uspto-grants-2016_02
- Patent number
- US09266864B2
Reaction notes
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