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