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

HRID 1194499

반응식

HRID 1194499 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매2회

실험 절차

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°.

후처리

  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)

출처 및 근거

ORD 기록
ord-923e4304ef314a089afc1df6a7a23b49
출처 데이터셋
uspto-grants-1989_03
특허 번호
US04814454

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