m-Chloroperbenzoic acid → 3-(Benzyloxy)-4-methoxyphenol

HRID 1684060Notes

Reaction equation

HRID 1684060 reaction equation
Cl[C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7]O)=O.COC1(C2C(C)[C:27]34C[CH:24]([O:25][C:26]3=[CH:33][C:32](=O)[C:31]([O:35]C)=[CH:30]4)C2)C=CC=C(OC)C1.CCCCCC.C(OCC)(=O)C>ClCCl.C(OCC)(=O)C>[CH2:5]([O:7][C:33]1[CH:32]=[C:31]([OH:35])[CH:30]=[CH:27][C:26]=1[O:25][CH3:24])[C:4]1[CH:3]=[CH:2][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 19041780HCID 19041780, compoundHCID 21226206Ethyl acetate hexane

Product 1

HCID 135310983-(Benzyloxy)-4-methoxyphenol

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-chloroperoxybenzoic acid (9.9 g, 0.0343 mols), in small portions, is added to a stirred solution of 3-benzyloxy-4-methoxybenzaldehyde (201, prepared as described in Example 66) (7.57 g, 0.0313 mols) in dicloromethane (100 ml) over a thirty minute period With vigorous shirring. The reaction flask is fitted with a condensor and the contents is heated to reflux for six hours and monitored by TLC using 2:1 hexane-ethyl acetate as eluant. The reaction is filtered off the 3-chlorobenzoic acid (which precipitates out of solution) and the filtrate is washed with saturated sodium bicarbonate followed by water and dried in vacuo to an oil which eventually solidifies. The solid is subsequently dissolved in distilled methanol (80 ml) and heated to reflux under nitrogen. TLC using hexane-ethyl acetate as the eluant shows almost complete conversion after two hours and forty five minutes. The solvent is removed in vacuo no produce a dark oil which is redissolved in a small amount of ethyl acetate and purified by column chromatography on silica gel (2:1 hexane-ethyl acetate as eluant). The major fraction from the column is combined and concentrated in vacuo to a solid (4.68 g, 64.9%).

Workup

  1. customThe reaction flask is fitted with a condensor
  2. temperaturethe contents is heated
  3. temperatureto reflux for six hours
  4. filtrationThe reaction is filtered off the 3-chlorobenzoic acid (which precipitates out of solution)
  5. washthe filtrate is washed with saturated sodium bicarbonate
  6. customdried in vacuo to an oil which
  7. dissolutionThe solid is subsequently dissolved in distilled methanol (80 ml)
  8. temperatureheated
  9. temperatureto reflux under nitrogen
  10. customafter two hours
  11. customforty five minutes
  12. customThe solvent is removed in vacuo
  13. customno produce a dark oil which
  14. custompurified by column chromatography on silica gel (2:1 hexane-ethyl acetate as eluant)
  15. concentrationconcentrated in vacuo to a solid (4.68 g, 64.9%)

Sources & evidence

ORD record
ord-eed3668b34b04ddc9606ac4654cdd2bb
Source dataset
uspto-grants-1997_06
Patent number
US05639782

Reaction notes

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