Reaktion #507936

ord-d8e7fb9e4deb49f58b3479ebbf6b83e1

Reaktionsgleichung

COC(=O)c1ccc(C)cc1Cl
Methyl 2-chloro-4-methylbenzoate
CC(C)[CH2][Al][CH2]C(C)C
Dibal-H
Cc1ccc(CO)c(Cl)c1
final compound
Ausbeute 82.6%
Cc1ccc(CO)c(Cl)c1
(2-chloro-4-methylphenyl)methanol
Ausbeute 82.6%

Lösungsmittel

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    workup.WAITThe mixture was left at 0° C. for 2H
  2. 2
    Sonstigeat room temperature
  3. 3
    Sonstigeovernight
  4. 4
    Sonstigereaction
  5. 5
    Sonstigewas quenched with Rochelle salt
  6. 6
    Sonstigeleaving
  7. 7
    Extraktionit was extracted with DCM
  8. 8
    Sonstigedried
  9. 9
    Einengenconcentrated

Vorschrift

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.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08097628B2uspto-grants-2012_01