Methanol → 2-Allylbenzylalcohol

Reaction equation

CC[O:3][CH2:4][CH3:5].O.[C:7]1([CH3:17])[CH:12]=[CH:11][C:10](S(O)(=O)=O)=[CH:9][CH:8]=1.[CH3:18]O>>[CH2:12]([C:11]1[CH:10]=[CH:9][CH:8]=[CH:18][C:5]=1[CH2:4][OH:3])[CH:7]=[CH2:17]

Participants

Reactant 3

HCID 887Methanol

HCID 3283Diethyl Ether

HCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 53150312-AllylbenzylalcoholYield 78%

Procedure

The crude THP ether B1-2 (18.54 g, 80 mmol) was dissolved in MeOH (160 mL) and p-toluenesulfonic acid monohydrate (PTSA, 1.52 g, 8 mmol) added. The resulting mixture was stirred at rt O/N, then concentrated under reduced pressure and the residue diluted with Et2O (100 mL). The organic layer was sequentially washed with 5% NaHCO3 (aq) solution (3×50 mL) and brine (1×50 mL), then dried over MgSO4. The solvent was evaporated under reduced pressure and the residue purified by flash chromatography (EtOAc/hexanes, 1:9), to obtain TB1 as a pale-yellow oil (9.2 g, 78%). TLC [EtOAc/hexanes (1:9), detection: UV, PMA; Rf=0.24]