Dimethyl Sulfoxide → 4-Formyl-2-methoxybenzoic acid

HRID 850163Notes

Reaction equation

HRID 850163 reaction equation
[OH:1][CH2:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[C:5]([O:12][CH3:13])[CH:4]=1.C(N(CC)CC)C.ClCCl.CS(C)=O>O>[CH:2]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[C:5]([O:12][CH3:13])[CH:4]=1)=[O:1]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 6344DichloromethaneHCID 8471TriethylamineHCID 212548144-(Hydroxymethyl)-2-methoxybenzoic acid

Product 1

HCID 212546644-Formyl-2-methoxybenzoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a mixture of 4-hydroxymethyl-2-methoxybenzoic acid (1.5 g), triethylamine (5 g), dichloromethane (3 ml) and dimethyl sulfoxide (3 ml) was added portionwise sulfur trioxide pyridine complex (3.93 g) in water bath, and the mixture was stirred for 1.5 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 evaporated in vacuo to give 4-formyl-2-methoxybenzoic acid.

Workup

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

Sources & evidence

ORD record
ord-67205a2f8f3940028afd417ff55e1db5
Source dataset
uspto-grants-2000_01
Patent number
US06015818

Reaction notes

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