m-Chloroperbenzoic acid → HCID 70157473, compound

HRID 843308Notes

Reaction equation

HRID 843308 reaction equation
[C:1]([O:5][C:6]([CH:8]1C=[C:12]2[CH2:14][CH:9]1[CH2:10][CH2:11]2)=[O:7])([CH3:4])([CH3:3])[CH3:2].ClC1C=C(C=CC=1)C(OO)=[O:20]>C(Cl)Cl>[C:1]([O:5][C:6]([CH:8]1[O:20][CH:12]2[CH2:14][CH:9]1[CH2:10][CH2:11]2)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 70158139HCID 70158139, compound2×

Product 1

HCID 70157473HCID 70157473, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Bicyclo[2.2.1]heptan-3-ene-2-carboxylic acid tert-butyl ester (1.94 g) is dissolved in CH2Cl2 (20 mL). m-Chloroperoxybenzoic acid (2.7 g, 70%) was added and the mixture was stirred 24 hrs. When bicyclo[2.2.1]heptan-3-ene-2-carboxylic acid tert-butyl ester disappeared, Na2CO3(sat.) (20 mL) was added then stirred for an additional 2 hrs. The reaction mixture was extracted with ethyl acetate (20 mL×3). The combined organic layers were washed till the pH=7 then evaporated to dryness to obtain the 3-oxa-bicyclo[2.2.1]heptan-2-carboxylic acid tert-butyl ester.

Workup

  1. stirringthen stirred for an additional 2 hrs
  2. extractionThe reaction mixture was extracted with ethyl acetate (20 mL×3)
  3. washThe combined organic layers were washed till the pH=7
  4. customthen evaporated to dryness

Sources & evidence

ORD record
ord-1e006da1233946dfb2501eee2e52467e
Source dataset
uspto-grants-2002_04
Patent number
US06376700B1

Reaction notes

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