Acetic Acid → (3-Methoxyphenylsulphanyl)acetaldehyde

HRID 252157Notes

Reaction equation

HRID 252157 reaction equation
C([O:3][CH:4](OCC)[CH2:5][S:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([O:13][CH3:14])[CH:8]=1)C.C(O)(=O)C>O>[CH3:14][O:13][C:9]1[CH:8]=[C:7]([S:6][CH2:5][CH:4]=[O:3])[CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 13642516(2,2-Diethoxyethyl)(3-methoxyphenyl)sulfane

Product 1

HCID 13642522(3-Methoxyphenylsulphanyl)acetaldehydeYield 92.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

1-(2,2-Diethoxyethylsulphanyl)-3-methoxybenzene (18 g, 70.21 mmol), glacial acetic acid (26 mL) and water (18 mL) were stirred at reflux temperature under nitrogen for 45 min. The reaction mixture was cooled to ambient temperature, diluted with water (180 mL) and extracted with tert-butyl methyl ether (3×40 mL). The combined extracts were cooled to <5° C. and washed with 5% aqueous sodium carbonate solution, water, and brine. The organic phase was dried (MgSO4) and concentrated in vacuo to yield the title compound (11.8 g, 92%).

Workup

  1. temperatureat reflux temperature under nitrogen for 45 min
  2. extractionextracted with tert-butyl methyl ether (3×40 mL)
  3. temperatureThe combined extracts were cooled to <5° C.
  4. washwashed with 5% aqueous sodium carbonate solution, water, and brine
  5. dry with materialThe organic phase was dried (MgSO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2313a955e56f48da80d0cd4c49ed95d2
Source dataset
uspto-grants-2011_01
Patent number
US07868017B2

Reaction notes

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