m-Chloroperbenzoic acid → 5-(Oxiran-2-yl)pentan-1-ol

HRID 1263273Notes

Reaction equation

HRID 1263273 reaction equation
[CH2:1]([OH:8])[CH2:2][CH2:3][CH2:4][CH2:5][CH:6]=[CH2:7].ClC1C=CC=C(C(OO)=[O:17])C=1>C(Cl)Cl.CCOCC>[O:8]1[CH2:1][CH:2]1[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][OH:17]

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 543123Hept-6-en-1-ol

Product 1

HCID 136166735-(Oxiran-2-yl)pentan-1-olYield 105%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 3 (1.4 g, 12 mmol) and m-chloroperbenzoic acid (2.92 g, 14.4 mmol) in methylene chloride (40 mL) was stirred at room temperature overnight. It was then diluted with ether, washed with saturated aqueous sodium bicarbonate, saturated aqueous sodium chloride, and dried over magnesium sulfate. Removal of the solvent afforded 1.64 g of the crude 6,7-epoxy-1-heptanol (5).

Workup

  1. washwashed with saturated aqueous sodium bicarbonate, saturated aqueous sodium chloride
  2. dry with materialdried over magnesium sulfate
  3. customRemoval of the solvent

Sources & evidence

ORD record
ord-5c79409ac5024472978391eca0fc0b90
Source dataset
uspto-grants-1984_06
Patent number
US04456613

Reaction notes

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