Water → 3-(Benzyloxy)-5-methoxybenzaldehyde

HRID 709675Notes

Reaction equation

HRID 709675 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH2:17][OH:18])[CH:12]=[C:13]([O:15][CH3:16])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.I(C1C=CC=CC=1C(O)=O)(=O)=O.O>CS(C)=O>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:12]=[C:13]([O:15][CH3:16])[CH:14]=1)[CH:17]=[O:18])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 1087942-Iodoxybenzoic acidHCID 696443123-Methoxy-5-(phenylmethoxy)benzenemethanol

Product 1

HCID 38487103-(Benzyloxy)-5-methoxybenzaldehydeYield 85.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of (3-(benzyloxy)-5-methoxyphenyl)methanol (6.50 g) in DMSO (100 mL) was added 2-iodoxybenzoic acid (9.00 g), and the mixture was stirred at room temperature for 3 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (5.50 g) as an oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-a756f0b0c2d54c2aae1e4b88a0b5becb
Source dataset
uspto-grants-2015_11
Patent number
US09181186B2

Reaction notes

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