1-Naphthol → HCID 20517366, compound

HRID 328888Notes

Reaction equation

HRID 328888 reaction equation
[CH:1]([N:5]1[CH2:8][CH:7]([OH:9])[CH2:6]1)([CH2:3][CH3:4])[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-].[Na+]>>[C:10]1([O:20][CH2:6][CH:7]([OH:9])[CH2:8][NH:5][CH:1]([CH2:3][CH3:4])[CH3:2])[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 3

HCID 70051-NaphtholHCID 14798Sodium HydroxideHCID 205173831-(1-Methylpropyl)-3-azetidinol

Product 1

HCID 20517366HCID 20517366, compoundYield 57%

Conditions

Temperature
160 °C

Procedure

To a mixture of 14.2 parts of 1-(sec.-butyl-3-azetidinol and 14.4 parts of α-naphthol 0.2 part of sodium hydroxide was added and the mixture was heated under nitrogen gas at 160° C. for 22 hours. The reaction mixture was cooled and then extracted with ether. The extract was washed with 2N-NaOH aqueous solution and then with water. The liquid was dried over anhydrous sodium sulfate and the solvent was distilled off. Recrystallization of the residue gave 15.5 parts of 1-(α-naphthoxy)-3-(sec.-butylamino)-2-propanol melting at 57°-59° C. The yield was 57%.

Workup

  1. additionwas added
  2. temperatureThe reaction mixture was cooled
  3. extractionextracted with ether
  4. washThe extract was washed with 2N-NaOH aqueous solution
  5. dry with materialThe liquid was dried over anhydrous sodium sulfate
  6. distillationthe solvent was distilled off
  7. customRecrystallization of the residue

Sources & evidence

ORD record
ord-c98a98829b754cf5b58e24ee459cdcd4
Source dataset
uspto-grants-1977_04
Patent number
US04018824

Reaction notes

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