3-Hydroxybenzaldehyde → 3-[(Methylsulfanyl)methoxy]benzaldehyde

HRID 1295735Notes

Reaction equation

HRID 1295735 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].C([O-])([O-])=O.[K+].[K+].[Na+].[I-].[CH3:18][S:19][CH2:20]Cl>CC(C)=O>[CH3:18][S:19][CH2:20][O:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6]

Participants

6

Reactant 4

HCID 1013-HydroxybenzaldehydeHCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 16916Chloromethyl methyl sulfide

Product 1

HCID 714171123-[(Methylsulfanyl)methoxy]benzaldehydeYield 36.31%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

3-Hydroxybenzaldehyde (6.106 g, 50.00 mmol) was dissolved in acetone at room temperature. K2CO3 (13.821 g, 100.00 mmol), NaI (7.569 g, 50.00 mmol) and chloromethyl methyl sulfide (4.19 mL, 50.00 mmol) were added, and the mixture was allowed to stir for 80 h. The mixture was filtered, the filtrate concentrated to an oil, and the residue purified by SiO2 eluted with 99:1 CH2Cl2/MeOH to give 3.309 g (36.31%) of a yellow oil.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate concentrated to an oil
  3. customthe residue purified by SiO2
  4. washeluted with 99:1 CH2Cl2/MeOH

Sources & evidence

ORD record
ord-ab9bf3afdb284b5498c7c3dd59d15d9d
Source dataset
uspto-grants-2007_07
Patent number
US07244738B2

Reaction notes

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