m-Chloroperbenzoic acid → 3-Chlorobenzoic Acid

HRID 2271088Notes

Reaction equation

HRID 2271088 reaction equation
C1C2C=CCCCC=2C=CC=1.[Cl:12][C:13]1[CH:14]=[C:15]([CH:20]=[CH:21][CH:22]=1)[C:16]([O:18]O)=[O:17]>C(Cl)Cl>[Cl:12][C:13]1[CH:14]=[C:15]([CH:20]=[CH:21][CH:22]=1)[C:16]([OH:18])=[O:17]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 5822646,7-Dihydro-5H-benzocycloheptene

Product 1

HCID 4473-Chlorobenzoic AcidYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a cold (0° C.) solution of 6,7-dihydro-5H-benzocycloheptene (0.915 g, 6.35 mmol) in methylene chloride (20 ml) was added 75% meta-chloro-peroxybenzoic acid (1.75 g, 7.63 mmol). The reaction mixture was allowed to come to room temperature over an 18 hour period. The reaction mixture was diluted with methylene chloride and washed with saturated sodium hydrogen carbonate solution, dried over MgSO4, filtered and evaporated to give the epoxide as a colorless oil (1.16 g, >100% yield, contaminated with meta-chlorobenzoic acid).

Workup

  1. washwashed with saturated sodium hydrogen carbonate solution
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-02de40dd2fa64e2caa5263fc816698d8
Source dataset
uspto-grants-2001_12
Patent number
US06333349B1

Reaction notes

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