Triethylamine → 4-Fluoro-2-methoxybenzaldehyde

HRID 636752Notes

Reaction equation

HRID 636752 reaction equation
C(N(CC)CC)C.[F:8][C:9]1[CH:16]=[CH:15][C:12]([CH2:13][OH:14])=[C:11]([O:17][CH3:18])[CH:10]=1.S(=O)(=O)=O.N1C=CC=CC=1.OS([O-])(=O)=O.[K+]>CS(C)=O>[F:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=[O:14])=[C:11]([O:17][CH3:18])[CH:10]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 168533Sulfur trioxide-pyridineHCID 516920Potassium bisulfateHCID 17750770(4-Fluoro-2-methoxyphenyl)methanol

Product 1

HCID 27745374-Fluoro-2-methoxybenzaldehydeYield 96%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Triethylamine (0.84 ml, 6.03 mmol) was added to a solution of 4-fluoro-2-methoxybenzylalcohol (310.8 mg, 1.99 mmol) in DMSO (7 ml). Pyridine sulfur trioxide (938.6 mg, 5.90 mmol) was added portionwise to the mixture checking raise of the temperature. The mixture was stirred for 1 hour. The mixture was added to 5% KHSO4 aqueous solution, extracted three times with ethyl acetate and dried over MgSO4. The mixture was concentrated and purified by silica gel chromatography (hexane/ether=5/1) to give the title compound (293.3 mg; 96%).

Workup

  1. temperaturechecking raise of the temperature
  2. extractionextracted three times with ethyl acetate
  3. dry with materialdried over MgSO4
  4. concentrationThe mixture was concentrated
  5. custompurified by silica gel chromatography (hexane/ether=5/1)

Sources & evidence

ORD record
ord-815cabe160d44fea837e419af1dcccb8
Source dataset
uspto-grants-2001_02
Patent number
US06194461B1

Reaction notes

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