Ammonium Chloride → 4-(Hydroxymethyl)-2-methylphenol

HRID 1269596

Reaktionsgleichung

Reaktionsgleichung von HRID 1269596
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[CH3:10].[B-].CCCC[N+](CCCC)(CCCC)CCCC.[Cl-].[NH4+]>C(Cl)Cl>[OH:7][CH2:6][C:5]1[CH:8]=[CH:9][C:2]([OH:1])=[C:3]([CH3:10])[CH:4]=1

Komponenten

5

Edukt 3

HCID 25517Ammonium Chloride2×HCID 1399014-Hydroxy-3-methylbenzaldehydeHCID 9881569Tetra-N-butylammonium borohydride

Produkt 1

HCID 142518564-(Hydroxymethyl)-2-methylphenolAusbeute 78,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 4-hydroxy-3-methylbenzaldehyde (10 g, 73.5 mmol) in dry CH2Cl2 (550 mL) under nitrogen at 5° C. was added tetra-N-butylammonium borohydride (20.58 g, 80 mmol) and the resultant mixture stirred for 1.25 h at 5° C. Saturated ammonium chloride solution (30 mL) was added to the reaction mixture and the resultant mixture stirred for 1 h at 5° C. Saturated ammonium chloride solution (60 mL) was added and the reaction mixture extracted with CH2Cl2, dried (Na2SO4) and the solvents removed in vacuo. Purification by flushing through silica (2×150 g) eluting with EtOAc afforded the title compound as an oily yellow solid (8.01 g).

Aufarbeitung

  1. extractionthe reaction mixture extracted with CH2Cl2
  2. dry with materialdried (Na2SO4)
  3. customthe solvents removed in vacuo
  4. customPurification
  5. customby flushing through silica (2×150 g)
  6. washeluting with EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-65f961eafc8b4085a7dad5f5dd583874
Quelldatensatz
uspto-grants-2007_04
Patentnummer
US07199239B2

Verknüpfte Notizen

Wird geladen…