m-Chloroperbenzoic acid → HCID 12252638, compound

HRID 899623Notes

Reaction equation

HRID 899623 reaction equation
[C:1]([O:4][CH2:5][CH2:6][CH:7]=[CH2:8])(=[O:3])[CH3:2].ClC1C=C(C=CC=1)C(OO)=[O:14]>ClCCl>[C:1]([O:4][CH2:5][CH2:6][CH:7]1[O:14][CH2:8]1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 740953-Buten-1-ol, 1-acetate

Product 1

HCID 12252638HCID 12252638, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-buten-1-yl acetate (5.7 g, 50 mmol) in dichloromethane (200 mL) was added m-chloroperoxybenzoic acid (12.9 g, 75 mmol). The reaction was then stirred at room temperature for 3 hours. The reaction mixture was then filtered through celite and concentrated in vacuo. The residue was purified by silica gel flash chromatography (4:1 hexanes:ethyl acetate) to yield 3,4-epoxybutan-1-yl acetate as a colourless oil in a yield of 3.8 g (58%). 1H NMR (CDCl3) δ 1.78-1.88 (m, 2H), 2.03 (s, 3H), 2.47 (m, 1H), 2.75 (m, 1H), 2.99 (m, 1H), 4.18 (t, 1H, J=6.6 Hz).

Workup

  1. filtrationThe reaction mixture was then filtered through celite and
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by silica gel flash chromatography (4:1 hexanes:ethyl acetate)

Sources & evidence

ORD record
ord-6383fcc0818c48b0b391ac491dc60398
Source dataset
uspto-grants-2008_04
Patent number
US07354932B2

Reaction notes

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