m-Chloroperbenzoic acid → 3-(2-Methoxyphenyl)-4,5-methylenedioxyphenol

HRID 860532Notes

Reaction equation

HRID 860532 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:10]=[C:11]([CH:14]=[C:15]2[O:19][CH2:18][O:17][C:16]=12)C=O.ClC1C=CC=C(C(OO)=[O:28])C=1>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:10]=[C:11]([OH:28])[CH:14]=[C:15]2[O:19][CH2:18][O:17][C:16]=12

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 865860323-(2-Methoxyphenyl)-4,5-methylenedioxybenzaldehyde

Product 1

HCID 695838203-(2-Methoxyphenyl)-4,5-methylenedioxyphenolYield 68%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-(2-methoxyphenyl)-4,5-methylenedioxybenzaldehyde (0.850 g, 3.32 mmol), m-chloroperbenzoic acid (1.431 g, 8.29 mmol) in CH2Cl2 (25 mL) was heated to reflux overnight. The resulting orange mixture was evaporated, dissolved into MeOH (15 mL) and 2.5 M NaOH (6 mL) and stirred for 45 minutes. The dark mixture was diluted with ethyl acetate and acidified with 1.0 N HCl. The layers were separated and the organics washed successively with water, 0.5 M NaHCO3, water, brine and dried (MgSO4). The mixture was filtered, evaporated and the residue was purified on silica gel (hexane:ethyl acetate 4:1) to give 0.55 g of 3-(2-methoxyphenyl)-4,5-methylenedioxyphenol (68%) as a tan solid, 1H NMR (500 MHz; CDCl3): δ 3.82 (s, 3H); 5.91 (s, 2H); 6.40–6.45 (m, 2H); 6.99 (d, J=9.0 Hz, 1H); 7.02 (d, J=7.0 Hz, 1H); 7.40–7.30 (m, 2H).

Workup

  1. temperatureto reflux overnight
  2. customThe resulting orange mixture was evaporated
  3. dissolutiondissolved into MeOH (15 mL) and 2.5 M NaOH (6 mL)
  4. additionThe dark mixture was diluted with ethyl acetate
  5. customThe layers were separated
  6. washthe organics washed successively with water, 0.5 M NaHCO3, water, brine
  7. dry with materialdried (MgSO4)
  8. filtrationThe mixture was filtered
  9. customevaporated
  10. customthe residue was purified on silica gel (hexane:ethyl acetate 4:1)

Sources & evidence

ORD record
ord-e25e1ebbf214476e9a3112ad3c80430b
Source dataset
uspto-grants-2006_12
Patent number
US07153875B2

Reaction notes

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