Dimethyl Sulfoxide → 4-Acetamido-3-methoxybenzaldehyde

HRID 613596Notes

Reaction equation

HRID 613596 reaction equation
[C:1]([NH:4][C:5]1[CH:12]=[CH:11][C:8]([CH2:9][OH:10])=[CH:7][C:6]=1[O:13][CH3:14])(=[O:3])[CH3:2].C(N(CC)CC)C.CS(C)=O.ClCCl>O>[C:1]([NH:4][C:5]1[CH:12]=[CH:11][C:8]([CH:9]=[O:10])=[CH:7][C:6]=1[O:13][CH3:14])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 6344DichloromethaneHCID 8471TriethylamineHCID 538917484-Acetamido-3-methoxybenzyl alcohol

Product 1

HCID 183218014-Acetamido-3-methoxybenzaldehydeYield 82.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a mixture of 4-acetamido-3-methoxybenzyl alcohol (800 mg), triethylamine (2.07 g), dimethylsulfoxide (5 ml) and dichloromethane (2.5 ml) was added portionwise sulfur trioxide pyridine complex (1.3 g) in water bath, and the mixture was stirred for 2 hours at the same temperature. The reaction mixture was poured into water, and extracted with dichloromethane. The organic layer was washed with water and brine, dried over magnesium sulfate and concentrated in vacuo to give 4-acetamido-3-methoxybenzaldehyde (653 mg).

Workup

  1. extractionextracted with dichloromethane
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-dd0bd5bd6f924a87aaf90e16d9644088
Source dataset
uspto-grants-1999_12
Patent number
US06008229

Reaction notes

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