Sodium Sulfite → HCID 66336272, compound

HRID 2066625Notes

Reaction equation

HRID 2066625 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[CH2:12]([O:19][C:20]1[CH:25]=[CH:24][C:23]([O:26][CH2:27][C:28]([CH3:30])=[CH2:29])=[CH:22][CH:21]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[O-]S([O-])=O.[Na+].[Na+]>C(Cl)Cl>[CH2:12]([O:19][C:20]1[CH:21]=[CH:22][C:23]([O:26][CH2:27][C:28]2([CH3:30])[CH2:29][O:9]2)=[CH:24][CH:25]=1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 24437Sodium SulfiteHCID 70297m-Chloroperbenzoic acidHCID 66957184HCID 66957184, compound

Product 1

HCID 66336272HCID 66336272, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Chloroperbenzoic acid (1.43 g of 50%, 4.14 mmol) was added to an ice-cooled mixture of 94 (500 mg, 1.97 mmol) and powdered Na2HPO4 (974 mg, 6.86 mmol) in CH2Cl2 (20 mL), and the resulting mixture was stirred at room temperature for 3.5 h. Cold aqueous Na2SO3 (50 mL of 10%) was added, and the mixture was extracted with CH2Cl2 (3×50 mL). The extracts were sequentially washed with cold aqueous Na2SO3 (50 mL of 10%), aqueous NaHCO3 (50 mL) and brine (50 mL). The combined extracts were then evaporated to dryness and the residue was chromatographed on silica gel. Elution with 25% CH2Cl2/petroleum ether firstly gave foreruns, and then further elution with 25-33% CH2Cl2/petroleum ether gave 2-{[4-(benzyloxy)phenoxy]methyl}-2-methyloxirane (95) (460 mg, 87%) as a white solid: mp (CH2Cl2/pentane) 105-107° C.; 1H NMR (CDCl3) δ 7.44-7.28 (m, 5H), 6.90 (dt, J=9.3, 2.9 Hz, 2H), 6.85 (dt, J=9.3, 2.9 Hz, 2H), 5.01 (s, 2H), 3.97 (d, J=10.5 Hz, 1H), 3.90 (d, J=10.5 Hz, 1H), 2.85 (d, J=4.8 Hz, 1H), 2.71 (d, J=4.8 Hz, 1H), 1.47 (s, 3H). Anal. (C17H18O3) C, H, N.

Workup

  1. temperaturecooled
  2. extractionthe mixture was extracted with CH2Cl2 (3×50 mL)
  3. washThe extracts were sequentially washed with cold aqueous Na2SO3 (50 mL of 10%), aqueous NaHCO3 (50 mL) and brine (50 mL)
  4. customThe combined extracts were then evaporated to dryness
  5. customthe residue was chromatographed on silica gel
  6. washElution with 25% CH2Cl2/petroleum ether firstly gave foreruns
  7. washfurther elution with 25-33% CH2Cl2/petroleum ether

Sources & evidence

ORD record
ord-73af876cf7344913b52e1197548df132
Source dataset
uspto-grants-2012_10
Patent number
US08293734B2

Reaction notes

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