Hydrochloric Acid → 5-(4-Chloro-benzyloxy)-2-methyl-phenol

HRID 2426126Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2426126
[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([CH2:6][O:7][C:8]2[CH:15]=[CH:14][C:11]([CH:12]=O)=[C:10]([OH:16])[CH:9]=2)=[CH:4][CH:3]=1.C([BH3-])#N.[Na+].CN(C1C=CC(N=NC2C=CC(S(O)(=O)=O)=CC=2)=CC=1)C.Cl>O1CCCC1.O>[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([CH2:6][O:7][C:8]2[CH:15]=[CH:14][C:11]([CH3:12])=[C:10]([OH:16])[CH:9]=2)=[CH:4][CH:3]=1

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 11037Benzenesulfonic acid, 4-(2-(4-(dimethylamino)phenyl)diazenyl)-HCID 5003444Sodium cyanoborohydrideHCID 861018764-(4-Chloro-benzyloxy)-2-hydroxybenzaldehyde

Produkt 1

HCID 575815955-(4-Chloro-benzyloxy)-2-methyl-phenol

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 4-(4-chloro-benzyloxy)-2-hydroxybenzaldehyde (1.31 g, 5.0 mmol) and sodium cyanoborohydride (1.0 g, 15.9 mmol, Aldrich) in tetrahydrofuran (30 mL) was added methyl orange as an indicator, giving the solution a yellow color; 1N aqueous HCl solution (7.5 mL) was added slowly, keeping the solution orange. The mixture was then stirred overnight at room temperature. Water was added, and the mixture was extracted with ethyl acetate three times. The combined organic phase was washed with water and brine, dried (MgSO4) and concentrated. The residue was purified by flash chromatography eluting with 0-40% ethyl acetate in hexanes to give 5-(4-chloro-benzyloxy)-2-methyl-phenol. (Yield 0.43 g).

Aufarbeitung

  1. customgiving the solution a yellow color
  2. extractionthe mixture was extracted with ethyl acetate three times
  3. washThe combined organic phase was washed with water and brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography
  7. washeluting with 0-40% ethyl acetate in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-a83cca2808f54cb987d886436135e624
Quelldatensatz
uspto-grants-2011_06
Patentnummer
US07968554B2

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