Dimethyl Sulfoxide → 4-Acetamido-3-methoxybenzaldehyde

HRID 1871096Notes

Reaction equation

HRID 1871096 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-31f1a0915a824bc4a69ee1b134c48f8f
Source dataset
uspto-grants-2000_08
Patent number
US06100284

Reaction notes

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