Water → 5-(Benzyloxy)-2-methylbenzaldehyde

HRID 709688Notes

Reaction equation

HRID 709688 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH3:17])=[C:13]([CH2:15][OH: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]=[CH:11][C:12]([CH3:17])=[C: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 117759998(5-(Benzyloxy)-2-methylphenyl)methanol

Product 1

HCID 600256215-(Benzyloxy)-2-methylbenzaldehydeYield 90.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of (5-(benzyloxy)-2-methylphenyl)methanol (280 mg) in DMSO (5.0 ml) was added 2-iodoxybenzoic acid (343 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 (250 mg) as a pale-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-d75b2eb0b2ea4e06b83120188ee9f9ee
Source dataset
uspto-grants-2015_11
Patent number
US09181186B2

Reaction notes

Loading…