m-Chloroperbenzoic acid → 2-Allyloxy-4-(benzyloxy)phenol

HRID 1267244Notes

Reaction equation

HRID 1267244 reaction equation
[CH2:1]([O:4][C:5]1[CH:12]=[C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:10]=[CH:9][C:6]=1C=O)[CH:2]=[CH2:3].ClC1C=C(C=CC=1)C(OO)=[O:26]>C(Cl)Cl>[CH2:1]([O:4][C:5]1[CH:12]=[C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:10]=[CH:9][C:6]=1[OH:26])[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 185460182-Allyloxy4-(benzyloxy)benzaldehyde

Product 1

HCID 185460122-Allyloxy-4-(benzyloxy)phenolYield 64.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a solution of 53.6 g (0.20 mole) of 2-allyloxy-4-(benzyloxy)benzaldehyde in 500 mL of methylene chloride was added a solution of 90 g (˜0.3 mole) of 57-86% m-chloroperoxybenzoic acid in 500 mL of methylene chloride. The mixture was stirred at room temperature for 3 days. It was then diluted to 2 L with methylene chloride and washed four times with 500 mL portions of saturated aqueous sodium bicarbonate, dried over magnesium sulfate, filtered and concentrated in vacuum to a brown oil. This was redissolved in 1 L of methanol, 110 g of basic alumina added and the mixture stirred at room temperature for 15 hours. The alumina was removed by filtration and the filtrate concentrated to 50 g of a yellow solid. The crude solid was column chromatographed on silica gel with hexane/methylene chloride as eluant to give 33 g of the title compound as a white solid, m.p. 62° C.

Workup

  1. washwashed four times with 500 mL portions of saturated aqueous sodium bicarbonate
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuum to a brown oil
  5. dissolutionThis was redissolved in 1 L of methanol
  6. addition110 g of basic alumina added
  7. stirringthe mixture stirred at room temperature for 15 hours
  8. customThe alumina was removed by filtration
  9. concentrationthe filtrate concentrated to 50 g of a yellow solid
  10. customchromatographed on silica gel with hexane/methylene chloride as eluant

Sources & evidence

ORD record
ord-e045baf0e9ed47daa9efaf19375fca1a
Source dataset
uspto-grants-2003_04
Patent number
US06552049B2

Reaction notes

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