Water → 3-Methoxy-5-methylbenzaldehyde

HRID 709722Notes

Reaction equation

HRID 709722 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:10][OH:11])[CH:6]=[C:7]([CH3:9])[CH:8]=1.I(C1C=CC=CC=1C(O)=O)(=O)=O.C(OCC)(=O)C.O>CS(C)=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:6]=[C:7]([CH3:9])[CH:8]=1)[CH:10]=[O:11]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 1087942-Iodoxybenzoic acidHCID 11030016(3-Methoxy-5-methylphenyl)methanol

Product 1

HCID 110947973-Methoxy-5-methylbenzaldehydeYield 92.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of (3-methoxy-5-methylphenyl)methanol (2.20 g) in DMSO (15 mL) was added 2-iodoxybenzoic acid (4.00 g), and the mixture was stirred at room temperature for 2 hr. Ethyl acetate (50 ml) and water (10 mL) were 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 to give the title compound (2.00 g) as a yellow oil. This compound was used for the next step without further purification.

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

Sources & evidence

ORD record
ord-a3528c941ef3495dacb3184c8d7d0c4d
Source dataset
uspto-grants-2015_11
Patent number
US09181186B2

Reaction notes

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