Isopropanol → (2-Methylsulfanylphenyl)methanol
Reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10][CH3:11].[H-].C([Al+]CC(C)C)C(C)C.CC(O)C.C(C(C(C([O-])=O)O)O)([O-])=O.[Na+].[K+]>C1(C)C=CC=CC=1>[CH3:11][S:10][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[CH2:3][OH:2]Participants
6
Conditions
- Temperature
- 0 °C
Procedure
To a solution of 2-methylsulfanylbenzoic acid methyl ester (0.30 g, 1.7 mmol) in toluene (3.0 mL), diisobutylaluminum hydride (0.94 mol/L toluene solution, 3.9 mL, 3.7 mmol) was added dropwise at −78° C. and the solution was stirred for 3.5 hours. The reaction mixture was added with 2-propanol (0.20 mL), warmed to 0° C., and added with saturated aqueous potassium sodium tartrate solution to separate the mixture into organic layer and aqueous layer. The obtained organic layer was concentrated under reduced pressure and the residue was purified by silica gel chromatography (hexane/ethyl acetate=90/10 to 70/30) to obtain (2-methylsulfanylphenyl)methanol (0.22 g, 87%).
Workup
- customto separate the mixture into organic layer and aqueous layer
- concentrationThe obtained organic layer was concentrated under reduced pressure
- customthe residue was purified by silica gel chromatography (hexane/ethyl acetate=90/10 to 70/30)
Sources & evidence
- ORD record
- ord-b23d453984154667bfaaa84e7354ce25
- Source dataset
- uspto-grants-2009_10
- Patent number
- US07605272B2
Reaction notes
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