m-Chloroperbenzoic acid → 3-Chlorobenzoic Acid

HRID 1072217Notes

Reaction equation

HRID 1072217 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-aa8a1ac9a9bd431593ad9375034e811d
Source dataset
uspto-grants-2005_06
Patent number
US06908947B2

Reaction notes

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