Isopropanol → 2-Isopropoxy-5-methylsulfonylbenzoic acid
Reaction equation
Cl[C:2]1[CH:10]=[CH:9][C:8]([S:11]([CH3:14])(=[O:13])=[O:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH:15]([OH:18])([CH3:17])[CH3:16]>CCN(CC)CC>[CH:15]([O:18][C:2]1[CH:10]=[CH:9][C:8]([S:11]([CH3:14])(=[O:13])=[O:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5])([CH3:17])[CH3:16]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 120 °C
Procedure
A mixture of 2.13 mmol 2-chloro-5-methanesulfonyl-benzoic acid, 0.64 mmol Cu(I)Br in 5 ml NEt3 and 25 ml isopropanol was heated to 120° C. for 16 h in a sealed tube. The volatiles were removed under vacuum, and the residue was taken up in 70 ml 1N HCl. Extraction with ethyl acetate drying of the combined organic fractions, and evaporation yielded a residue which was purified by reversed phase preparative HPLC eluting with an acetonitrile/water gradient. Evaporation of the product fractions yielded the title compound
Workup
- customThe volatiles were removed under vacuum
- extractionExtraction with ethyl acetate
- customdrying of the combined organic fractions, and evaporation
- customyielded a residue which
- customwas purified by reversed phase preparative HPLC
- washeluting with an acetonitrile/water gradient
- customEvaporation of the product fractions
Sources & evidence
- ORD record
- ord-dbc52edea3cf4af2b9c2c196c3f5fd2b
- Source dataset
- uspto-grants-2008_09
- Patent number
- US07429585B2
Reaction notes
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