Potassium Hydroxide → 2-(Benzylsulfanyl)benzoic acid

HRID 11309

Reaction equation

HRID 11309 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(3X), 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(3X)
  5. dry with materialdried with MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give a white solid

Sources & evidence

ORD record
ord-5efd89b5050f46a987a88ade1df59f7b
Source dataset
uspto-grants-2006_08
Patent number
US07098223B2

Linked notes

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