Sodium Bicarbonate → 5-[3-(Methyloxy)propyl]-2-(methylthio)benzaldehyde

HRID 337624Notes

Reaction equation

HRID 337624 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][C:6]1[CH:7]=[CH:8][C:9]([S:14][CH3:15])=[C:10]([CH:13]=1)[CH2:11][OH:12].C(=O)(O)[O-].[Na+]>ClCCl>[CH3:1][O:2][CH2:3][CH2:4][CH2:5][C:6]1[CH:7]=[CH:8][C:9]([S:14][CH3:15])=[C:10]([CH:13]=1)[CH:11]=[O:12]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 668961945-[3-(Methyloxy)propyl]-2-(methylthio)benzyl alcohol

Product 1

HCID 866516765-[3-(Methyloxy)propyl]-2-(methylthio)benzaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a dichloromethane solution of 5-[3-(methyloxy)propyl]-2-(methylthio)benzyl alcohol (1 eq.) from the previous step was added sodium bicarbonate (5 eq.) and DMP (1.1 eq.). The resulting reaction suspension was stirred for 1.5 h at RT. The reaction was quenched with sat. aq. NaHSO3 and then extracted with dichloromethane. The combined organic extracts were washed further with 1 N aq. NaOH, water and brine, dried over MgSO4 and filtered. Concentration of the filtrate in vacuo afforded the crude title compound as a colorless oil.

Workup

  1. customThe resulting reaction suspension
  2. customThe reaction was quenched with sat. aq. NaHSO3
  3. extractionextracted with dichloromethane
  4. washThe combined organic extracts were washed further with 1 N aq. NaOH, water and brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered

Sources & evidence

ORD record
ord-95c948786c924e05815c79085a226f01
Source dataset
uspto-grants-2014_11
Patent number
US08889714B2

Reaction notes

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