Safrole → Safrole oxide

HRID 1270644

Reaction equation

HRID 1270644 reaction equation
[O:1]1[C:12]2[C:4](=[CH:5][C:6](=[CH:10][CH:11]=2)[CH2:7][CH:8]=[CH2:9])[O:3][CH2:2]1.ClC1C=C(C=CC=1)C(OO)=[O:18]>C(Cl)Cl>[O:1]1[C:12]2[C:4](=[CH:5][C:6](=[CH:10][CH:11]=2)[CH2:7][CH:8]2[O:18][CH2:9]2)[O:3][CH2:2]1

Participants

4

Reactant 2

HCID 5144SafroleHCID 70297m-Chloroperbenzoic acid

Product 1

HCID 101123Safrole oxide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Safrole oxide was prepared by stirring a solution of safrole (1.48 mL, 10 mmol) and m-chloroperoxybenzoic acid (2.70 g, 11 mmol) in methylene dichloride (25 mL) overnight. The reaction was quenched by pouring into water (50 mL). The aqueous was extracted with ether (3×25 mL). The organic layers were combined and washed with 10% aqueous sodium sulfate (2×25 mL), saturated aqueous sodium bicarbonate (3×25 mL), and brine (25 mL). The organic phase was dried over magnesium sulfate and the solvents were removed in vacuo. The resulting yellow oil was used without further purification.

Workup

  1. customThe reaction was quenched
  2. additionby pouring into water (50 mL)
  3. extractionThe aqueous was extracted with ether (3×25 mL)
  4. washwashed with 10% aqueous sodium sulfate (2×25 mL), saturated aqueous sodium bicarbonate (3×25 mL), and brine (25 mL)
  5. dry with materialThe organic phase was dried over magnesium sulfate
  6. customthe solvents were removed in vacuo
  7. customThe resulting yellow oil was used without further purification

Sources & evidence

ORD record
ord-c03c854e78a447c992e058552ddbc863
Source dataset
uspto-grants-2007_04
Patent number
US07202261B2

Linked notes

Loading…