3-Hydroxybenzaldehyde → 3-[[(3-Phenoxyphenyl)amino]methyl]phenol

HRID 990553Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 990553
[O:1]([C:8]1[CH:9]=[C:10]([CH:12]=[CH:13][CH:14]=1)[NH2:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:15][C:16]1[CH:17]=[C:18]([CH:21]=[CH:22][CH:23]=1)[CH:19]=O.C(O)(=O)C.[OH-].[Na+]>ClCCCl>[O:1]([C:8]1[CH:9]=[C:10]([NH:11][CH2:19][C:18]2[CH:21]=[CH:22][CH:23]=[C:16]([OH:15])[CH:17]=2)[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

6

Edukt 4

HCID 1013-HydroxybenzaldehydeHCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 771353-Phenoxyaniline

Produkt 1

HCID 109462273-[[(3-Phenoxyphenyl)amino]methyl]phenolAusbeute 69,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 111,2-DichloroethaneLösungsmittel

Versuchsvorschrift

The 3-(phenoxy)aniline (555 mg, 3 mmol) and 3-hydroxybenzaldehyde (366 mg, 3 mmol) were dissolved in 7 mL of 1,2-dichloroethane. Acetic acid (0.189 mL 3.15 mmol) and solid NaBr(OAc)3 (1.01 g, 5 mmol) were added. The mixture was stirred at room temperature for 3 h, then acidified with 1NHCl solution. After neutralizing to pH 7.5 with 2.5 N sodium hydroxide, the mixture was extracted with methylene chloride. The organic layer was washed with brine and water, then dried over anhydrous MgSO4, and evaporated to give 609 mg (69%) of the desired N-(3-phenoxyphenyl)[[3-hydroxyphenyl]methyl]amine product as a brown oil, which was greater than 90% pure by reverse phase HPLC analysis. MS m/z=291.

Aufarbeitung

  1. extractionthe mixture was extracted with methylene chloride
  2. washThe organic layer was washed with brine and water
  3. dry with materialdried over anhydrous MgSO4
  4. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-3a620d197f80459e8243171685b94795
Quelldatensatz
uspto-grants-2002_10
Patentnummer
US06458852B1

Notizen zur Reaktion

Wird geladen…