Dimethyl Sulfoxide → 4-Methoxy-3,5-dimethylbenzaldehyde

HRID 2231115Notes

Reaction equation

HRID 2231115 reaction equation
[CH3:1][O:2][C:3]1[C:10]([CH3:11])=[CH:9][C:6]([CH2:7][OH:8])=[CH:5][C:4]=1[CH3:12].C(Cl)(=O)C(Cl)=O.CS(C)=O.C(N(CC)CC)C>C(Cl)Cl>[CH3:1][O:2][C:3]1[C:4]([CH3:12])=[CH:5][C:6]([CH:7]=[O:8])=[CH:9][C:10]=1[CH3:11]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 2758574HCID 2758574, compound

Product 1

HCID 27585734-Methoxy-3,5-dimethylbenzaldehydeYield 94.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The aldehyde was synthesized according to the procedure of Example 46, Step 1 using the alcohol from Step 2 (7.5 g, 45 mmol), oxalyl chloride (6.35 g, 50 mmol), dimethylsulfoxide (8.8 g, 100 mmol) and triethylamine (10.2 g, 110 mmol) and in methylene chloride (100 ml). There was obtained 7 g (92%) of the desired aldehyde which was used in the next step without further purification.

Workup

  1. customThe aldehyde was synthesized

Sources & evidence

ORD record
ord-e0086035a1674424834efe0944aee7f0
Source dataset
uspto-grants-2002_07
Patent number
US06426360B1

Reaction notes

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