Potassium Hydroxide → 2-(Benzylsulfanyl)benzoic acid

HRID 545974

Reaction equation

HRID 545974 reaction equation
C([O:8][C:9](=[O:24])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[S:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)C1C=CC=CC=1.[OH-].[Na+].[OH-].[K+]>>[CH2:17]([S:16][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[C:9]([OH:24])=[O:8])[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

4

Reactant 3

HCID 14797Potassium HydroxideHCID 14798Sodium HydroxideHCID 802018Benzyl 2-(benzylsulfanyl)benzoate

Product 1

HCID 2641822-(Benzylsulfanyl)benzoic acid

Procedure

To a suspension of 2-benzylsulfanyl benzoic acid benzyl ester 2 (113 mg, 0.34 mmol) was added 1.6 mL of 1N NaOH. KOH (1 pellet) was added and the reaction was continued overnight. The acetone was removed and a small amount of water was added. The aqueous solution was washed with CH2Cl2 (3×). The aqueous phase was acidified until pH of 2-3 was reached then extracted with CH2Cl2 (3×), dried with MgSO4 and filtered and concentrated to give a white solid.

Workup

  1. customThe acetone was removed
  2. additiona small amount of water was added
  3. washThe aqueous solution was washed with CH2Cl2 (3×)
  4. extractionwas reached then extracted with CH2Cl2 (3×)
  5. dry with materialdried with MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give a white solid

Sources & evidence

ORD record
ord-7396428940c1476d9c1702a8b2a38f8a
Source dataset
uspto-grants-2011_05
Patent number
US07935825B2

Linked notes

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