p-Toluenesulfonic acid → HCID 18670342, compound

HRID 1915995Notes

Reaction equation

HRID 1915995 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5](C=O)=[C:4]([O:10][CH3:11])[CH:3]=1.CO[CH:14]([O:17][CH3:18])[O:15][CH3:16].C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)([O-])[O-].[K+].[K+]>CO>[CH3:18][O:17][CH:14]([O:15][CH3:16])[C:5]1[CH:8]=[CH:9][C:2]([Br:1])=[CH:3][C:4]=1[O:10][CH3:11]

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 9005Trimethyl orthoformateHCID 11430Potassium CarbonateHCID 110530414-Bromo-2-methoxybenzaldehyde

Product 1

HCID 18670342HCID 18670342, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-bromo-2-methoxybenzaldehyde (5.2 g, 24.2 mmol) in methanol (20 ml) and trimethylorthoformate (14 ml, 5.5 eq.) was added p-toluenesulfonic acid (46 mg, 0.01 eq.) and the mixture was refluxed for 3 hr. Potassium carbonate (125 mg, 0.03 eq.) and silicagel was added, the solvent was removed under reduced pressure and the solid residue packed into a loading column and purified by MPLC (hexanes-ethylacetate 40-80% gradient). MS (EI+): 262, 260 (1/1, M+, 10%); 231, 229 (1/1, 90%); 215, 213 (1/1, 10%); 199, 170, 150, 118, 92, 75, 45 (100%).

Workup

  1. temperaturethe mixture was refluxed for 3 hr
  2. customthe solvent was removed under reduced pressure
  3. custompurified by MPLC (hexanes-ethylacetate 40-80% gradient)

Sources & evidence

ORD record
ord-66d508b00ce146e1bb1cc9e28a5dd14a
Source dataset
uspto-grants-2013_12
Patent number
US08617515B2

Reaction notes

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