Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → Ethyl 3-(4-hydroxyphenyl)butanoate

HRID 2101806Notes

Reaction equation

HRID 2101806 reaction equation
O1CCCCC1[O:7][C:8]1[CH:13]=[CH:12][C:11]([CH:14]([CH3:21])[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]([CH:14]([CH3:21])[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 57672398Ethyl 3-(4-(tetrahydro-2H-pyran-2-yloxy)phenyl)butanoate

Product 1

HCID 51349438Ethyl 3-(4-hydroxyphenyl)butanoateYield 84.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of 38.1 (5.00 g, 17.1 mmol) in EtOH (100 mL) at room temperature was added PPTS. The resulting solution was stirred for 16 hours and then concentrated in vacuo. The residue was purified by flash chromatography (SiO2 gel 60, eluted with 0%-20% EtOAc in hexanes). Fractions containing the desired product were combined and concentrated to give 38.2 (3.00 g, 84%) as a colorless oil. MS ESI (pos.) m/e: 226.1 (M+H2O)+.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified by flash chromatography (SiO2 gel 60, eluted with 0%-20% EtOAc in hexanes)
  3. additionFractions containing the desired product
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-bd34c74cfe7040ccb2ac11d559c4b163
Source dataset
uspto-grants-2009_08
Patent number
US07572934B2

Reaction notes

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