Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → HCID 57672372, compound

HRID 2101775Notes

Reaction equation

HRID 2101775 reaction equation
O1CCCCC1[O:7][C:8]1[CH:13]=[CH:12][C:11]([C@H:14](/[CH:21]=[CH:22]/[CH2:23][CH3:24])[CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:10][CH:9]=1.CC1C=CC(S([O-])(=O)=O)=CC=1.C1C=C[NH+]=CC=1>CCO>[OH:7][C:8]1[CH:9]=[CH:10][C:11]([C@H:14](/[CH:21]=[CH:22]/[CH2:23][CH3:24])[CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 57672482HCID 57672482, compound

Product 1

HCID 57672372HCID 57672372, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of 18.1 (180 mg, 0.57 mmol) in EtOH (5 mL) at 23 C was added PPTS (catalytic). Stirring was continued for 16 hours. The reaction was concentrated in vacuo. The residue was then purified by flash chromatography (SiO2 gel 60, eluted with 0 to 20% EtOAc in hexanes). Fractions containing the desired product were combined and concentrated to give a colorless oil. The residue was purified by flash chromatography (SiO2 gel 60, eluted with 0 to 20% EtOAc in hexanes). The combined fractions were concentrated under reduced pressure to afford phenol 18.2 (120 mg, 89%) as a colorless oil.

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. customThe residue was then purified by flash chromatography (SiO2 gel 60, eluted with 0 to 20% EtOAc in hexanes)
  3. additionFractions containing the desired product
  4. concentrationconcentrated
  5. customto give a colorless oil
  6. customThe residue was purified by flash chromatography (SiO2 gel 60, eluted with 0 to 20% EtOAc in hexanes)
  7. concentrationThe combined fractions were concentrated under reduced pressure

Sources & evidence

ORD record
ord-0c148feb0f844d3f925b8a7ea7d12a67
Source dataset
uspto-grants-2009_08
Patent number
US07572934B2

Reaction notes

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