Water → HCID 15657627, compound

HRID 1197527Notes

Reaction equation

HRID 1197527 reaction equation
O[C:2]1([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]([CH3:12])[CH2:4][CH2:3]1.C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1(C)C=CC=CC=1>[CH3:12][CH:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:2]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:3][CH2:4]1

Participants

5

Reactant 3

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 15657621HCID 15657621, compound

Product 1

HCID 15657627HCID 15657627, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The compound from Example 27 (42 g, 0.18 mole) and p-toluenesulfonic acid (6 g) were dissolved in 500 mL toluene and heated at reflux for 30 minutes with removal of water (Dean-Stark trap). The solution was cooled and washed with saturated sodium bicarbonate, dried over sodium sulfate, filtered and evaporated. The residual syrup was chromatographed on silica gel (0-3% ethyl acetate in heptane) to give the title compound in 93% yield.

Workup

  1. temperatureheated
  2. temperatureThe solution was cooled
  3. washwashed with saturated sodium bicarbonate
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residual syrup was chromatographed on silica gel (0-3% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-dce5a5b61388467d83f7d0d8dc492e98
Source dataset
uspto-grants-1994_01
Patent number
US05276053

Reaction notes

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