p-Toluenesulfonic acid → HCID 71292050, compound

HRID 1481687Notes

Reaction equation

HRID 1481687 reaction equation
[C:1]([C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13](=O)[CH3:14])=[C:8]([OH:16])[CH:7]=1)(=[O:5])[CH2:2][CH2:3][CH3:4].CC1C=CC(S(O)(=O)=O)=CC=1>>[CH3:14][C:13]1[O:16][C:8]2[CH:7]=[C:6]([C:1](=[O:5])[CH2:2][CH2:3][CH3:4])[CH:11]=[CH:10][C:9]=2[N:12]=1

Participants

3

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 71281758HCID 71281758, compound

Product 1

HCID 71292050HCID 71292050, compoundYield 35.1%

Conditions

Temperature
160 °C

Procedure

To a suspension of N-(4-butyryl-2-hydroxyphenyl)acetamide (0.81 g, 3.7 mmol) in xylenes (3 mL) was added p-TsOH (0.7 g, 3.7 mmol, 1.0 eq) at room temperature then the mixture was heated to 160° C. and stirred overnight. The solvent was removed under reduced pressure then saturated aqueous NaHCO3 was added and the biphasic mixture was extracted by CH2Cl2 (4×20 mL). The solvent was concentrated to give a crude product which was purified by flash column chromatography (0-25% EtOAc in hexanes) to afford the title compound as a light yellow solid (262 mg, 1.3 mmol, 35%).

Workup

  1. customThe solvent was removed under reduced pressure
  2. additionsaturated aqueous NaHCO3 was added
  3. extractionthe biphasic mixture was extracted by CH2Cl2 (4×20 mL)
  4. concentrationThe solvent was concentrated
  5. customto give a crude product which
  6. customwas purified by flash column chromatography (0-25% EtOAc in hexanes)

Sources & evidence

ORD record
ord-fc2ed77d94b14950acaf7b9073333902
Source dataset
uspto-grants-2016_08
Patent number
US09409905B2

Reaction notes

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