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

HRID 2198833Notes

Reaction equation

HRID 2198833 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
160 °C

Procedure

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 2 N-sodium hydroxide aqueous solution and extracted three times with 50 parts of 2 N-hydrochloric acid aqueous solution. The extract was washed with 50 parts of ether and made alkaline by addition of 2 N-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 hydrochloride 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.

Workup

  1. additionwas added
  2. temperatureThe reaction mixture was cooled
  3. washThe solution was washed twice with 50 parts of 2 N-sodium hydroxide aqueous solution
  4. extractionextracted three times with 50 parts of 2 N-hydrochloric acid aqueous solution
  5. washThe extract was washed with 50 parts of ether
  6. additionby addition of 2 N-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

Sources & evidence

ORD record
ord-a2a36132d6c944758bec72d343aa9803
Source dataset
uspto-grants-1982_11
Patent number
US04360464

Reaction notes

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