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

HRID 1017033Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1017033
[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.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].Cl.[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

8

Edukt 6

HCID 1013-HydroxybenzaldehydeHCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 771353-PhenoxyanilineHCID 5049666Sodium triacetoxyborohydride

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 111,2-DichloroethaneLösungsmittel

Versuchsvorschrift

EX-655A) 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 NaBH(OAc)3 (1.01 g, 5 mmol) were added. The mixture was stirred at room temperature for 3 h, then acidified with 1 N HCl 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-7f3c13975c3442f8990b40d48f4d3e8e
Quelldatensatz
uspto-grants-2002_11
Patentnummer
US06476057B1

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