Sodium borohydride → {4-[2-(2,6-Dichloro-4-methylphenoxy)ethoxy]phenyl}methanol

HRID 2194861Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2194861
[Cl:1][C:2]1[CH:19]=[C:18]([CH3:20])[CH:17]=[C:16]([Cl:21])[C:3]=1[O:4][CH2:5][CH2:6][O:7][C:8]1[CH:15]=[CH:14][C:11]([CH:12]=[O:13])=[CH:10][CH:9]=1.[BH4-].[Na+]>C1COCC1.CO>[Cl:1][C:2]1[CH:19]=[C:18]([CH3:20])[CH:17]=[C:16]([Cl:21])[C:3]=1[O:4][CH2:5][CH2:6][O:7][C:8]1[CH:15]=[CH:14][C:11]([CH2:12][OH:13])=[CH:10][CH:9]=1

Komponenten

4

Edukt 2

HCID 4311764Sodium borohydrideHCID 579560774-[2-(2,6-Dichloro-4-methylphenoxy)ethoxy]benzaldehyde

Produkt 1

HCID 67447508{4-[2-(2,6-Dichloro-4-methylphenoxy)ethoxy]phenyl}methanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21899815MeOH tetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of the aldehyde from Step 2 (1 eq.) in a mixture of THF/MeOH (2/1, 0.21M) was added portion wise sodium borohydride (1.5 eq.). The mixture was stiffed 3 h at room temperature, quenched slowly with 1N HCl and finally concentrated in vacuo. The residual aqueous phase was extracted with diethylether twice. The combined organic extracts were washed with brine, dried over MgSO4, filtered and concentrated. Stirring the residue in 10% Et2O/Hex for 4 h followed by filtration afforded the desired alcohol as a white crystalline solid.

Aufarbeitung

  1. customquenched slowly with 1N HCl
  2. concentrationfinally concentrated in vacuo
  3. extractionThe residual aqueous phase was extracted with diethylether twice
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. filtrationfollowed by filtration

Quellen und Nachweise

ORD-Eintrag
ord-062e222120974d5cb3fbde44196a10f5
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08334308B2

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