Chavicol → (RS)-4-Oxiranylmethyl-phenol

HRID 1419931Notes

Reaction equation

HRID 1419931 reaction equation
[CH2:1]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)[CH:2]=[CH2:3].C([O-])(O)=[O:12].[Na+].ClC1C=CC=C(C(OO)=O)C=1>C(Cl)Cl>[O:12]1[CH2:3][CH:2]1[CH2:1][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 68148ChavicolHCID 70297m-Chloroperbenzoic acid2×HCID 516892Sodium Bicarbonate2×

Product 1

HCID 53757927(RS)-4-Oxiranylmethyl-phenolYield 38%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-allylphenol (8.9 g, 66.3 mmol) was dissolved in CH2Cl2 (180 ml). After addition of NaHCO3 (8.4 g, 99.5 mmol), m-chloroperbenzoic acid 70% (18 g, 73 mmol) was added portionwise. After 6 hours at room temperature, additional NaHCO3 (8.4 g, 99.5 mmol) and m-chloroperbenzoic acid 70% (18 g, 73 mmol) were added. After 17 hours, the reaction mixture was washed with sat. NaHCO3 (200 ml) and the resulting aqueous phases were extracted with CH2Cl2 (3×10 ml). The combined organic phases were washed with sat. Na2S2O3 (2×100 ml), dried over Na2SO4 and concentrated. The residue was chromatographed over silica gel (hexan-ethyl acetate 9:1 then 1:1) to provide (RS)-4-oxiranylmethyl-phenol (3.77 g, 38%) as yellow solid, m.p. 54°-57° C. and MS: m/e=150 (M+).

Workup

  1. additionwas added portionwise
  2. waitAfter 17 hours
  3. washthe reaction mixture was washed with sat. NaHCO3 (200 ml)
  4. extractionthe resulting aqueous phases were extracted with CH2Cl2 (3×10 ml)
  5. washThe combined organic phases were washed with sat. Na2S2O3 (2×100 ml)
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated
  8. customThe residue was chromatographed over silica gel (hexan-ethyl acetate 9:1

Sources & evidence

ORD record
ord-379d6fd19a694e2aa763f16a3d92ebe2
Source dataset
uspto-grants-1999_03
Patent number
US05889026

Reaction notes

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