Potassium Hydroxide → HCID 9818974, compound

HRID 722788Notes

Reaction equation

HRID 722788 reaction equation
C([S:4][CH2:5][CH2:6][C:7]1[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([C:25]([O:27]C)=[O:26])=[CH:21][CH:20]=2)[C:8]=1[C:9]([O:11]C)=[O:10])(=O)C.[OH-].[K+]>CCO>[C:25]([C:22]1[CH:21]=[CH:20][C:19]([CH2:18][O:17][C:13]2[CH:14]=[CH:15][CH:16]=[C:7]([CH2:6][CH2:5][SH:4])[C:8]=2[C:9]([OH:11])=[O:10])=[CH:24][CH:23]=1)([OH:27])=[O:26]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 20728721HCID 20728721, compound

Product 1

HCID 9818974HCID 9818974, compoundYield 46.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a deoxygenated solution of 2-[2-(acetylthio)ethyl]-6-[4-(methoxycarbonyl)phenyl]methoxy-benzoic acid, methyl ester (0.20 g, 0.50 mmol) in 95% EtOH (3 mL) was added a deoxygenated solution of KOH (0.463 g, 8.3 mmol) in 95% EtOH (3 mL) under nitrogen. The solution was heated at reflux overnight and quenched by addition of 1 N HCl (20 mL). The mixture was extracted with EtOAc (3×20 mL) and the combined organic extracts were washed with water and brine, then dried over MgSO4, filtered, and concentrated. Purification by flash chromatography (1:1 dichloromathane/hexanes with 1% acetic acid) provided 2-[(4-Carboxyphenyl)methoxy]-6-(2-mercaptoethyl)-benzoic acid (0.077 g, 46%) as a white solid: 1H NMR (CD3OD) δ 2.75 (m, 2H), 2.92 (m, 2H), 5.22 (s, 2H), 6.93 (d, J=7.5 Hz, 1H), 6.98 (d, J=8.2 Hz, 1H), 7.30 (t, J=8.3 Hz, 1H), 7.55 (d, J=7.9 Hz, 2H), 8.02 (d, J=8.0 Hz, 2H); 13C NMR (CD3OD) δ 26.5, 39.8, 71.1, 112.4, 123.9, 126.9, 128.3, 131.3, 131.7, 131.8, 139.9, 144.2, 156.7, 170.0, 172.3. Anal. Calcd for C17H16O5S: C, 61.43; H, 4.85; S, 9.65. Found: C, 61.16; H, 4.95; S, 9.44.

Workup

  1. temperatureThe solution was heated
  2. temperatureat reflux overnight
  3. customquenched by addition of 1 N HCl (20 mL)
  4. extractionThe mixture was extracted with EtOAc (3×20 mL)
  5. washthe combined organic extracts were washed with water and brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customPurification by flash chromatography (1:1 dichloromathane/hexanes with 1% acetic acid)

Sources & evidence

ORD record
ord-a1f12b7e77c14e9e8228907188510daf
Source dataset
uspto-grants-2006_11
Patent number
US07138543B2

Reaction notes

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