Isopropanol → 2-Isopropoxy-5-methylsulfonylbenzoic acid

HRID 2117454Notes

Reaction equation

HRID 2117454 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

HCID 3776IsopropanolHCID 23291322-Chloro-5-(methylsulphonyl)benzoic acid

Product 1

HCID 211002372-Isopropoxy-5-methylsulfonylbenzoic acid

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

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

  1. customThe volatiles were removed under vacuum
  2. extractionExtraction with ethyl acetate
  3. customdrying of the combined organic fractions and evaporation
  4. customyielded a residue which
  5. customwas purified by reversed phase preparative HPLC
  6. washeluting with an acetonitrile/water gradient
  7. customEvaporation of the product fractions

Sources & evidence

ORD record
ord-543f14475d1c454894a1c3d35bb45bcf
Source dataset
uspto-grants-2008_10
Patent number
US07442710B2

Reaction notes

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