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

HRID 990553ノート

反応式

HRID 990553 の反応式
[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

参加物

6

反応物 4

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

生成物 1

HCID 109462273-[[(3-Phenoxyphenyl)amino]methyl]phenol収率 69.7%

試薬・触媒・溶媒 1

HCID 111,2-Dichloroethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-3a620d197f80459e8243171685b94795
出典データセット
uspto-grants-2002_10
特許番号
US06458852B1

反応ノート

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