p-Toluenesulfonic acid → HCID 21886104, compound

HRID 470334Notes

Reaction equation

HRID 470334 reaction equation
[Br:1][C:2]1[CH:9]=[C:6](C=O)[C:5]([OH:10])=[CH:4][CH:3]=1.[CH:11]([O:16][CH3:17])([O:14][CH3:15])OC.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)(O)[O-].[Na+]>>[Br:1][C:2]1[CH:9]=[CH:6][C:5]([OH:10])=[C:4]([CH:11]([O:14][CH3:15])[O:16][CH3:17])[CH:3]=1

Participants

5

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 9005Trimethyl orthoformateHCID 728635-BromosalicylaldehydeHCID 516892Sodium Bicarbonate

Product 1

HCID 21886104HCID 21886104, compound

Conditions

Temperature
-18 °C

Procedure

A mixture of 5-bromosalicylaldehyde (41.0 g, 0.200 mol), trimethyl orthoformate (205 ml, 1.83 mol) and dry p-toluenesulfonic acid (1.77 g, 0.010 mol) was refluxed for 24 h. After the reaction mixture was cooled to the RT, sodium bicarbonate (50 g) was carefully added, and the mixture was ultrasonicated for 5 min. The liquid was separated; the solid was washed with dry benzene (25 ml) and removed by filtration. Combined solutions were evaporated. The residue was triturated with dry hexane (30 ml) if necessary cooled to −18° C. Precipitate formed was collected by filtration, washed with dry hexane (20 ml). Slightly yellow crystals, 44.2 g (0.179 mol, 89%).

Workup

  1. temperaturewas refluxed for 24 h
  2. additionwas carefully added
  3. customthe mixture was ultrasonicated for 5 min
  4. customThe liquid was separated
  5. washthe solid was washed with dry benzene (25 ml)
  6. customremoved by filtration
  7. customCombined solutions were evaporated
  8. customThe residue was triturated with dry hexane (30 ml)
  9. customPrecipitate formed
  10. filtrationwas collected by filtration
  11. washwashed with dry hexane (20 ml)

Sources & evidence

ORD record
ord-842d0fad664c46398831844d92f3ca25
Source dataset
uspto-grants-2014_01
Patent number
US08629147B2

Reaction notes

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