m-Chloroperbenzoic acid → HCID 118024581, compound

HRID 1750546Notes

Reaction equation

HRID 1750546 reaction equation
[CH:1]1([O:6][CH2:7][C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=2)[CH2:5][CH:4]=[CH:3][CH2:2]1.ClC1C=C(C(OO)=[O:24])C=CC=1>C(Cl)Cl>[CH3:15][O:14][C:11]1[CH:10]=[CH:9][C:8]([CH2:7][O:6][CH:1]2[CH2:5][CH:4]3[CH:3]([O:24]3)[CH2:2]2)=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 118024523HCID 118024523, compound

Product 1

HCID 118024581HCID 118024581, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-[(cyclopent-3-en-1-yloxy)methyl]-4-methoxybenzene (9.64 g, 47.2 mmol) in dry DCM (52 ml) at 0° C. under an atmosphere of nitrogen was added 3-chlorobenzene-1-carboperoxoic acid (CAS number 937-14-4; 16.29 g, 94 mmol). The reaction mixture was warmed to room temperature for 17 hours then filtered. The filtrate was washed with a saturated solution of sodium thiosulfate and then with a saturated solution of sodium bicarbonate. The organics were dried over magnesium sulfate, filtered and concentrated in vacuo. The crude material was purified by column chromatography (silica, 0-50% ethyl acetate/petrol) to afford the title compound.

Workup

  1. filtrationthen filtered
  2. washThe filtrate was washed with a saturated solution of sodium thiosulfate
  3. dry with materialThe organics were dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude material was purified by column chromatography (silica, 0-50% ethyl acetate/petrol)

Sources & evidence

ORD record
ord-216a9e1864c040b9af6f20ea3da38f9e
Source dataset
uspto-grants-2015_10
Patent number
US09156829B2

Reaction notes

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