Ethanol → HCID 23093062, compound

HRID 1431022Notes

Reaction equation

HRID 1431022 reaction equation
C[O:2][C:3](=[O:25])[C:4]1[CH:9]=[C:8]([O:10][C:11]2[CH:16]=[CH:15][C:14]([S:17]([CH3:20])(=[O:19])=[O:18])=[CH:13][CH:12]=2)[CH:7]=[C:6]([O:21][CH:22]([CH3:24])[CH3:23])[CH:5]=1.CCO.O.[OH-].[Na+]>C1COCC1>[CH:22]([O:21][C:6]1[CH:5]=[C:4]([CH:9]=[C:8]([O:10][C:11]2[CH:16]=[CH:15][C:14]([S:17]([CH3:20])(=[O:19])=[O:18])=[CH:13][CH:12]=2)[CH:7]=1)[C:3]([OH:25])=[O:2])([CH3:24])[CH3:23]

Participants

6

Reactant 4

HCID 702EthanolHCID 962WaterHCID 14798Sodium HydroxideHCID 59649315HCID 59649315, compound

Product 1

HCID 23093062HCID 23093062, compoundYield 102.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-isopropoxy-5-(4-methanesulfonyl-phenoxy)-benzoic acid methyl ester (prepared as in Example 6 Step A) (6.50 g, 17.8 mmol) in THF (120 mL) was added EtOH (80 mL) and water (40 mL) at room temperature. Sodium hydroxide solution (1.0 M, 36.0 mL) was added slowly with some external cooling, if needed. The mixture was stirred at room temperature overnight. On the second day organic solvents were removed by evaporation. The residue was partitioned between ether and water. After the ether layer was discarded, the aqueous layer was acidified with HCl (6.0 M, ˜6.0 mL) to pH<2, and extracted with EtOAc three times. Combined EtOAc layers were washed with brine, dried with anhydrous MgSO4, filtered, and concentrated to give 3-isopropoxy-5-(4-methanesulfonyl-phenoxy)-benzoic acid (6.40 g, 100%) as a white solid. 1H NMR (300 MHz, CDCl3): δ 9.91 (s, 1H), 7.93 (d, J=9 Hz, 2H), 7.23 (m, 1H), 7.14 (d, J=9 Hz, 2H), 7.10 (m, 1H), 6.85 (m, 1H), 4.57-4.65 (m, 1H), 3.01 (s, 3H), 1.37 (d, J=6 Hz, 6H).

Workup

  1. customOn the second day organic solvents were removed by evaporation
  2. customThe residue was partitioned between ether and water
  3. extractionextracted with EtOAc three times
  4. washCombined EtOAc layers were washed with brine
  5. dry with materialdried with anhydrous MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-19100f8614a540a2a23c24fd6243c6a9
Source dataset
uspto-grants-2015_01
Patent number
US08940927B2

Reaction notes

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