Sodium Hydroxide → Benzoic Acid

HRID 2220233Notes

Reaction equation

HRID 2220233 reaction equation
[CH:1]1[CH:6]=[C:5](Cl)[CH:4]=[C:3]([C:8]([O:10]O)=[O:9])[CH:2]=1.[OH-].[Na+]>C(Cl)Cl>[C:8]([OH:10])(=[O:9])[C:3]1[CH:4]=[CH:5][CH:6]=[CH:1][CH:2]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 70297m-Chloroperbenzoic acid

Product 1

HCID 243Benzoic Acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of Example 349G in CH2Cl2 was treated with mCPBA and stirred at room temperature for seven hours. The mixture was then treated with 2M NaOH and the organic layer was separated, dried (Na2SO4), filtered through a pad of silica and concentrated. The resulting solid was crystallized from EtOH/H2O to afford a white solid contaminated with benzoic acid. The solid was dissolved in hot DMSO/EtOH and precipitated with water to afford the title compound (0.84 mg). HPLC Rt=4.03 min. m/z=412 (M+H+).

Workup

  1. customthe organic layer was separated
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered through a pad of silica
  4. concentrationconcentrated
  5. customThe resulting solid was crystallized from EtOH/H2O

Sources & evidence

ORD record
ord-34b7137b5ea14c2f9ea2509c0234d63e
Source dataset
uspto-grants-2008_08
Patent number
US07417040B2

Reaction notes

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