Ethyl Acetate → 3-(Benzyloxy)-4-methylbenzaldehyde

HRID 709659Notes

Reaction equation

HRID 709659 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH2:16][OH:17])[CH:12]=[CH:13][C:14]=1[CH3:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.I(C1C=CC=CC=1C(O)=O)(=O)=O.C(OCC)(=O)C>CS(C)=O>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:12]=[CH:13][C:14]=1[CH3:15])[CH:16]=[O:17])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 1087942-Iodoxybenzoic acidHCID 24721056[3-(Benzyloxy)-4-methylphenyl]methanol

Product 1

HCID 161013893-(Benzyloxy)-4-methylbenzaldehyde

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of (3-(benzyloxy)-4-methylphenyl)methanol (entire amount) in DMSO (15 mL) was added 2-iodoxybenzoic acid (3.20 g), and the mixture was stirred at room temperature for 2 hr. Ethyl acetate (250 mL) was added to the reaction mixture, and the insoluble material was filtered off. The filtrate 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 (2.50 g) as a yellow oil.

Workup

  1. filtrationthe insoluble material was filtered off
  2. washThe filtrate 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-08b4b0578b36493d9c7e9fbb0b8faf73
Source dataset
uspto-grants-2015_11
Patent number
US09181186B2

Reaction notes

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