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

HRID 1017033ノート

反応式

HRID 1017033 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.[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

参加物

8

反応物 6

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

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

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.

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-7f3c13975c3442f8990b40d48f4d3e8e
出典データセット
uspto-grants-2002_11
特許番号
US06476057B1

反応ノート

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