Hydrochloric Acid → HCID 21100220, compound

HRID 1352247Notes

Reaction equation

HRID 1352247 reaction equation
C[O:2][C:3](=[O:20])[C:4]1[CH:9]=[C:8]([S:10]([CH3:13])(=[O:12])=[O:11])[CH:7]=[CH:6][C:5]=1[O:14][CH2:15][CH:16]1[CH2:19][CH2:18][CH2:17]1.[OH-].[Na+].Cl>O1CCCC1>[CH:16]1([CH2:15][O:14][C:5]2[CH:6]=[CH:7][C:8]([S:10]([CH3:13])(=[O:12])=[O:11])=[CH:9][C:4]=2[C:3]([OH:20])=[O:2])[CH2:19][CH2:18][CH2:17]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 58677833HCID 58677833, compound

Product 1

HCID 21100220HCID 21100220, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To 6.51 mmol 2-cyclobutylmethoxy-5-methanesulfonyl-benzoic acid methyl ester in 20 ml tetrahydrofuran was added 40 mmol 2 N aq NaOH solution and the reaction mixture was stirred at 60° C. for 2 hours. After such time the reaction mixture was acidified by addition of concentrated HCl and extracted twice with dichloromethane. The combined organic phases were dried over sodium sulfate and concentrated in vacuo. The residue was triturated in ether to give the title compound as a white solid (40% over 2 steps). MS (m/e): 283.3 ([M−H]−, 100%).

Workup

  1. extractionextracted twice with dichloromethane
  2. dry with materialThe combined organic phases were dried over sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe residue was triturated in ether

Sources & evidence

ORD record
ord-0a6aca494db149379d34d017a330437d
Source dataset
uspto-grants-2007_05
Patent number
US07220744B2

Reaction notes

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