1-Naphthol → 1-(1-Naphthyloxy)-3-(tert-butylamino)-2-propanol

HRID 328882

반응식

HRID 328882 반응식
[C:1]([N:5]1[CH2:8][CH:7]([OH:9])[CH2:6]1)([CH3:4])([CH3:3])[CH3:2].[C:10]1([OH:20])[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:12][CH:11]=1.[OH-].[K+]>CCOCC>[C:10]1([O:20][CH2:6][CH:7]([OH:9])[CH2:8][NH:5][C:1]([CH3:2])([CH3:3])[CH3:4])[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:12][CH:11]=1

참가 물질

5

반응물 3

HCID 70051-NaphtholHCID 14797Potassium HydroxideHCID 2879861-tert-Butyl-3-hydroxyazetidine

생성물 1

HCID 100618521-(1-Naphthyloxy)-3-(tert-butylamino)-2-propanol

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

반응 조건

온도
160 °C

실험 절차

To a mixture of 6.5 parts of 1-(tert.-butyl)-3-azetidinol and 7.9 parts of α-naphthol 0.2 part of potassium hydroxide was added, and the mixture was heated at 160° C. for 24 hours. The reaction mixture was cooled and then dissolved in 100 parts of ether. The solution was washed twice with 50 parts of 2N-sodium hydroxide aqueous solution and extracted three times with 50 parts of 2N-hydrochloric acid aqueous solution. The extract was washed with 50 parts of ether and made alkaline by addition of 2N-sodium hydroxide aqueous solution. Extraction was conducted three times with 50 parts of benzene, and the extract was dried over anhydrous sodium sulfate. Then benzene was distilled off and the residue was solidified by drying under reduced pressure. The solid residue was subjected to distillation under reduced pressure. As a result 5 parts of 1-(α-naphthoxy)-3-(tert.-butylamino)-2-propanol boiling at 175°-180° C. under 1.5 mm Hg were obtained. A part of the product was dissolved in 5 parts of anhydrous ether and the product was converted to a hydrochloride by adding a hydrochloric acid gas to the resulting ether solution. The hydrochloric was recrystallized twice from a mixed solvent of ethyl acetate and ether. As a result 1-(α-naphthoxy)-3-(tert.-butylamino)-2-propanol hydrochloride having a melting point of 182°-184° C was obtained.

후처리

  1. additionwas added
  2. temperatureThe reaction mixture was cooled
  3. washThe solution was washed twice with 50 parts of 2N-sodium hydroxide aqueous solution
  4. extractionextracted three times with 50 parts of 2N-hydrochloric acid aqueous solution
  5. washThe extract was washed with 50 parts of ether
  6. additionby addition of 2N-sodium hydroxide aqueous solution
  7. extractionExtraction
  8. dry with materialthe extract was dried over anhydrous sodium sulfate
  9. distillationThen benzene was distilled off
  10. customby drying under reduced pressure
  11. distillationThe solid residue was subjected to distillation under reduced pressure

출처 및 근거

ORD 기록
ord-fc35e339cba841e2a629e0b44d2a1d83
출처 데이터셋
uspto-grants-1977_04
특허 번호
US04018824

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