Sodium Carbonate → 2-(2-Chlorobenzyl)oxirane

HRID 1988804Notes

Reaction equation

HRID 1988804 reaction equation
C1C=C(Cl)C=C(C(OO)=[O:9])C=1.[Cl:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH2:19][CH:20]=[CH2:21].C([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl>[Cl:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH2:19][CH:20]1[O:9][CH2:21]1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 70297m-Chloroperbenzoic acidHCID 5760611-Allyl-2-chlorobenzene

Product 1

HCID 123223492-(2-Chlorobenzyl)oxiraneYield 95.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

MCPBA (826 mg, 3.83 mmol) was added portionwise to an ice-cold solution of 2-chloro-1-allylbenzene (487 mg, 3.19 mmol) in CH2Cl2 (20 mL). The mixture was stirred at room temperature for 16 h. Aqueous 10% Na2CO3 solution (10 mL) and CH2Cl2 (100 mL) were added. The solution was successively washed with aqueous 10% Na2S2O3 (2×40 mL) and brine (40 mL), dried (MgSO4), filtered and concentrated under reduced pressure. The residue was purified by flash chromatography (hexane:EtOAc, 8:2) to give the title compound (512 mg, 95% yield).

Workup

  1. washThe solution was successively washed with aqueous 10% Na2S2O3 (2×40 mL) and brine (40 mL)
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by flash chromatography (hexane:EtOAc, 8:2)

Sources & evidence

ORD record
ord-7bd2bc0a5bfe4c1ea278f0ce421684b8
Source dataset
uspto-grants-2010_01
Patent number
US07642277B2

Reaction notes

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