Dibah → (2-Chloro-4-methylphenyl)methanol
Reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]([CH3:12])[CH:9]=[CH:8][C:3]=1[C:4](OC)=[O:5].CC(C[Al]CC(C)C)C>ClCCl>[Cl:1][C:2]1[CH:11]=[C:10]([CH3:12])[CH:9]=[CH:8][C:3]=1[CH2:4][OH:5]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Methyl 2-chloro-4-methylbenzoate (520 mg, 2.82 mmol) was dissolved in Dichloromethane (DCM) (15 mL) and at 0° C. Dibal-H (4.694 ml, 7.04 mmol) was slowly added. The mixture was left at 0° C. for 2H and then at room temperature overnight. Next morning HPLC showed no starting material remaining, reaction was quenched with Rochelle salt, and leaving under stirring for 1 hour and then it was extracted with DCM, dried and concentrated to afford 365 mg of the final compound, pure enough to be used in the next step.
Workup
- waitThe mixture was left at 0° C. for 2H
- customat room temperature
- customovernight
- customreaction
- customwas quenched with Rochelle salt
- customleaving
- extractionit was extracted with DCM
- customdried
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-d8e7fb9e4deb49f58b3479ebbf6b83e1
- Source dataset
- uspto-grants-2012_01
- Patent number
- US08097628B2
Reaction notes
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