1-Naphthol → HCID 13055702, compound

HRID 328885Notes

Reaction equation

HRID 328885 reaction equation
[CH2:1]([N:3]1[CH2:6][CH:5]([OH:7])[CH2:4]1)[CH3:2].[C:8]1([OH:18])[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=[CH:10][CH:9]=1.[OH-].[K+]>>[C:8]1([O:18][CH2:4][CH:5]([OH:7])[CH2:6][NH:3][CH2:1][CH3:2])[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 3

HCID 70051-NaphtholHCID 14797Potassium HydroxideHCID 138139281-Ethylazetidin-3-ol

Product 1

HCID 13055702HCID 13055702, compoundYield 70%

Conditions

Temperature
160 °C

Procedure

To a mixture of 10.2 parts of 1-ethyl-3-azetidinol and 14.4 parts of α-naphthol 0.2 part of potassium hydroxide was added, and the mixture was heated under nitrogen gas at 160° C. for 18 hours. The reaction mixture was cooled and extracted with ether. The ether extract was washed with 2N-NaOH aqueous solution and then with water. The liquor was dried over anhydrous sodium sulfate and the solvent was distilled off. The residue was recrystallized from cyclohexane to yield 17.2 parts of 1-(α-naphthoxy)-3-ethylamino-2-propanol. The melting of the product was 106°-107° C. The yield was 70%.

Workup

  1. additionwas added
  2. temperatureThe reaction mixture was cooled
  3. extractionextracted with ether
  4. extractionThe ether extract
  5. washwas washed with 2N-NaOH aqueous solution
  6. dry with materialThe liquor was dried over anhydrous sodium sulfate
  7. distillationthe solvent was distilled off
  8. customThe residue was recrystallized from cyclohexane

Sources & evidence

ORD record
ord-57e0804322d142c0a0c4f9d760ee75fd
Source dataset
uspto-grants-1977_04
Patent number
US04018824

Reaction notes

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