Water → HCID 23371782, compound

HRID 1899863Notes

Reaction equation

HRID 1899863 reaction equation
[Br:1][C:2]1[C:3]([CH3:15])=[CH:4][C:5]2[O:10][C:9]([CH3:12])([CH3:11])[CH2:8][CH:7](O)[C:6]=2[CH:14]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1(C)C=CC=CC=1>[Br:1][C:2]1[C:3]([CH3:15])=[CH:4][C:5]2[O:10][C:9]([CH3:11])([CH3:12])[CH:8]=[CH:7][C:6]=2[CH:14]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 23371774HCID 23371774, compound

Product 1

HCID 23371782HCID 23371782, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A stirred solution of the product of step d (27.1 g) in dry toluene (300 ml) is treated with p-toluenesulphonic acid (1.15 g) and heated under reflux for 2 h with water formed being removed via a Dean-Stark apparatus. The cooled solution is washed with aqueous sodium carbonate (100 ml, 2M), dried (Na2SO4), filtered and the solvent is evaporated off under reduced pressure to yield the crude product. This is purified by chromatography (silica gel, hexane) to give the title compound as an oil.

Workup

  1. temperatureheated
  2. customformed
  3. custombeing removed via a Dean-Stark apparatus
  4. washThe cooled solution is washed with aqueous sodium carbonate (100 ml, 2M)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customthe solvent is evaporated off under reduced pressure
  8. customto yield the crude product
  9. customThis is purified by chromatography (silica gel, hexane)

Sources & evidence

ORD record
ord-769b9c76fccc4fbaaadd6933345b24cb
Source dataset
uspto-grants-1996_11
Patent number
US05574049

Reaction notes

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