Methanol → 2-Allylbenzylalcohol

HRID 2096127Notes

Reaction equation

HRID 2096127 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

4

Reactant 3

HCID 887MethanolHCID 3283Diethyl EtherHCID 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]

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionthe residue diluted with Et2O (100 mL)
  3. washThe organic layer was sequentially washed with 5% NaHCO3 (aq) solution (3×50 mL) and brine (1×50 mL)
  4. dry with materialdried over MgSO4
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue purified by flash chromatography (EtOAc/hexanes, 1:9)

Sources & evidence

ORD record
ord-d4cb99b655dc42a1b2c2efb848efce94
Source dataset
uspto-grants-2013_05
Patent number
US08450268B2

Reaction notes

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