Water → HCID 86759950, compound

HRID 1744728Notes

Reaction equation

HRID 1744728 reaction equation
[CH2:1]([O:9][CH2:10][C:11]12[CH2:17][CH:14]([CH2:15][CH2:16]1)[CH:13]=[CH:12]2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].C(OO)(=[O:20])C.O>C(Cl)Cl>[CH2:1]([O:9][CH2:10][C:11]12[CH2:17][CH:14]([CH2:15][CH2:16]1)[CH:13]1[CH:12]2[O:20]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

5

Reactant 3

HCID 962WaterHCID 6585Peracetic AcidHCID 22222983HCID 22222983, compound

Product 1

HCID 86759950HCID 86759950, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A 500 mL round bottom flask equipped with a stirrer bar was charged with 14.3 g (0.056 mol) of 4-n-octyloxymethyl-bicyclo[2.2.1]hept-2-ene, and 80 mL of methylene choride. Peracetic acid (15.6 g, 35 wt. % in acetic acid; 0.072 mol) in methylene chloride (70 mL) was added dropwise to the above mixture over 20 min. in an ice bath. After the above mixture was reacted at room termperature for 3 hrs., 100 mL of water was added to the above reaction mixture, the organic layer was washed with saturated sodium carbonate solution (2×100 mL), then with water (2×100 mL), and dried with sodium sulfate. The solvent was evaporated and the residue was vacuum distilled to give pure product.

Workup

  1. customA 500 mL round bottom flask equipped with a stirrer bar
  2. customAfter the above mixture was reacted at room termperature for 3 hrs
  3. washthe organic layer was washed with saturated sodium carbonate solution (2×100 mL)
  4. dry with materialwith water (2×100 mL), and dried with sodium sulfate
  5. customThe solvent was evaporated
  6. distillationdistilled
  7. customto give pure product

Sources & evidence

ORD record
ord-342bec19bfc34f229e42fc8cbcd77068
Source dataset
uspto-grants-2006_03
Patent number
US07018559B2

Reaction notes

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