4-Aminophenol → 6-[(4-Hydroxyphenyl)amino]-2-naphthalenol

HRID 1194499

反応式

HRID 1194499 の反応式
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[OH:9][C:10]1[CH:19]=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[C:15](O)[CH:16]=2)[CH:11]=1.S(=O)(O)[O-].[Na+]>O>[OH:8][C:5]1[CH:6]=[CH:7][C:2]([NH:1][C:15]2[CH:16]=[C:17]3[C:12](=[CH:13][CH:14]=2)[CH:11]=[C:10]([OH:9])[CH:19]=[CH:18]3)=[CH:3][CH:4]=1

参加物

5

反応物 3

HCID 4034-AminophenolHCID 935522,6-DihydroxynaphthaleneHCID 23665763Sodium Bisulfite

生成物 1

HCID 144992086-[(4-Hydroxyphenyl)amino]-2-naphthalenol収率 31.1%

試薬・触媒・溶媒 1

HCID 962Water溶媒2 回

実験手順

A mixture of 300 mg (2.75 mmol, Aldrich) of 4-aminophenol, 1.5 g (90%, 8.4 mmol, Aldrich) of 2,6-dihydroxynaphthalene and 1.0 g (9.6 mmol, Aldrich), of sodium bisulfite in 30 ml of H2O was refluxed for 18 hours. The reaction mixture was cooled, added to 30 ml of H2O and extracted with two 25 ml portions of ethyl acetate. The organic extracts were combined, dried (MgSO4), and concentrated in vacuo to give a solid. The crude solid was purified by flash chromatography (15×5.0 cm, 1:2 EtOAc/pet ether) followed by recrystallization (EtOAc/pet ether) to afford 215 mg (31%) of title compound as pale pink crystals, m.p. 195°-196°.

後処理

  1. temperatureThe reaction mixture was cooled
  2. extractionextracted with two 25 ml portions of ethyl acetate
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customto give a solid
  6. customThe crude solid was purified by flash chromatography (15×5.0 cm, 1:2 EtOAc/pet ether)
  7. customfollowed by recrystallization (EtOAc/pet ether)

出典と根拠

ORDレコード
ord-923e4304ef314a089afc1df6a7a23b49
出典データセット
uspto-grants-1989_03
特許番号
US04814454

関連ノート

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