Dichloromethane → HCID 18753066, compound

HRID 870490Notes

Reaction equation

HRID 870490 reaction equation
[CH:1]([C:3]1[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=1[C:5]#[N:6])=[CH2:2].C(=O)(O)[O-:12].[Na+].ClCCl.C1C=C(Cl)C=C(C(OO)=O)C=1>O>[O:12]1[CH2:2][CH:1]1[C:3]1[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=1[C:5]#[N:6]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 122378792-Ethenylbenzonitrile

Product 1

HCID 18753066HCID 18753066, compoundYield 13.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Into a 100-mL round-bottom flask was placed 2-ethenylbenzonitrile (2.73 g, 21.14 mmol, 1.00 equiv), sodium bicarbonate (1.77 g, 21.07 mmol, 4.61 equiv), dichloromethane (20 mL) and water (20 mL). Then m-CPBA (10.9 g, 63.16 mmol, 2.25 equiv) was added at 0° C. in several batches. The resulting solution was stirred overnight at room temperature and then concentrated under vacuum. The residue was applied onto a silica gel column with PE/EA (50:1). Purification afforded 400 mg (13%) of 2-(oxiran-2-yl)benzonitrile as a yellow oil.

Workup

  1. customInto a 100-mL round-bottom flask was placed
  2. concentrationconcentrated under vacuum
  3. customPurification

Sources & evidence

ORD record
ord-84d0e66b2a374681ac47a0b0ac37d7c6
Source dataset
uspto-grants-2015_03
Patent number
US08969557B2

Reaction notes

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