Water → 3-(Benzyloxy)-2-methylbenzaldehyde

HRID 709706Notes

Reaction equation

HRID 709706 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([CH3:17])=[C:11]([CH2:15][OH:16])[CH:12]=[CH:13][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[C:10]([CH3:17])=[C:11]([CH:12]=[CH:13][CH:14]=1)[CH:15]=[O:16])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 1087942-Iodoxybenzoic acidHCID 58087471(3-Benzyloxy-2-methyl-phenyl)-methanol

Product 1

HCID 159481993-(Benzyloxy)-2-methylbenzaldehydeYield 88.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of (3-(benzyloxy)-2-methylphenyl)methanol (228 mg) in DMSO (5.0 mL) was added 2-iodoxybenzoic acid (280 mg), and the mixture was stirred at room temperature for 2 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 to give the title compound (200 mg) as a yellow oil. This compound was used for the next step without further purification.

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

Sources & evidence

ORD record
ord-8495db2b503142098448647d9c175e7a
Source dataset
uspto-grants-2015_11
Patent number
US09181186B2

Reaction notes

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