Isopropanol → 2-Isopropoxy-5-methylsulfonylbenzoic acid

HRID 1930973Notes

Reaction equation

HRID 1930973 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]>C(N(CC)CC)C>[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 triethylamine and 25 ml isopropanol was heated to 120° C. for 16 h in a sealed tube. The volatiles were removed in vacuo and the residue was taken up in 70 ml 1 N 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. MS (m/e): 257.0 ([M−H]−, 100%)

Workup

  1. customThe volatiles were removed in vacuo
  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-671014d39e51435cbb2e49fd47e9d212
Source dataset
uspto-grants-2012_05
Patent number
US08188139B2

Reaction notes

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