3-Hydroxybenzaldehyde → 3-(2-Methylthioethoxy)benzaldehyde

HRID 641822Notes

Reaction equation

HRID 641822 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH:7]=[O:8].[CH3:12][S:13][CH2:14][CH2:15]Cl>CN(C=O)C>[CH3:12][S:13][CH2:14][CH2:15][O:3][C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH:7]=[O:8]

Participants

5

Reactant 3

HCID 1013-HydroxybenzaldehydeHCID 109652-Chloroethyl methyl sulfideHCID 24758Sodium hydride

Product 1

HCID 231317123-(2-Methylthioethoxy)benzaldehyde

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

NaH (1.3 g, 54 mmol) is added to a solution of 5.0 g (41 mmol) 3-hydroxybenzaldehyde in 30 ml DMF at 0° C. After stirring for 1 h 4.44 ml (45 mmol) 2-chloroethyl methyl sulphide is added. The reaction mixture is warmed to room temperature and stirring is continued for 16 h. Then the reaction mixture is poured onto water and extracted with ethyl acetate. The combined organic layers are washed with water and brine, dried over MgSO4, filtered and concentrated in vacuo. The residue is purified by flash-chromatography on silica gel (hexane/EtOAc=3:1) to afford the title compound as a colorless oil.

Workup

  1. additionis added
  2. additionThen the reaction mixture is poured onto water
  3. extractionextracted with ethyl acetate
  4. washThe combined organic layers are washed with water and brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue is purified by flash-chromatography on silica gel (hexane/EtOAc=3:1)

Sources & evidence

ORD record
ord-e9aff6c2260e4def8dd4a97cb691424a
Source dataset
uspto-grants-2010_04
Patent number
US07696216B2

Reaction notes

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