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1-Butanol → 2-(6-Octyloxy-2-naphthyl)-5-butylbenzooxazole

HRID 5284
Notes
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Reaction equation

HRID 5284 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:12]1[O:13][C:14]3[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][CH2:23][CH3:24])=[CH:17][C:15]=3[N:16]=1)[CH:6]=[CH:5]2.[CH2:25](I)[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32].[OH-].[K+].C(O)CCC>O>[CH2:25]([O:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:12]1[O:13][C:14]3[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][CH2:23][CH3:24])=[CH:17][C:15]=3[N:16]=1)[CH:6]=[CH:5]2)[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 2631-ButanolHCID 123801-IodooctaneHCID 14797Potassium HydroxideHCID 1357271132-(6-Hydroxy-2-naphthyl)-5-butylbenzooxazole

Product 1

HCID 197954142-(6-Octyloxy-2-naphthyl)-5-butylbenzooxazoleYield 56.6%

Reagents, catalysts & solvents 1

HCID 962
Water
Solvent

Procedure

In a 30ml round-bottom flask, 0.47 g (1.48 m mole) of 2-(6-hydroxy-2-naphthyl)-5-butylbenzooxazole, 0.43 g (1.79 m mole) of octyl iodide, 0.12 g (1.82 m mole) of potassium hydroxide and 5 ml of butanol were placed, followed by refluxing for 310 minutes. The reaction mixture was poured into water, extracted from ethyl acetate to obtain an organic layer. The organic layer was washed with water dried with mirabilite and dried under reduced pressure to obtain a resultant. The resultant was recrystallized from ethylacetate to obtain a crystal. The crystal was filtered, purified by silica gel column chromatography (eluent: toluene) and recrystallized from acetone to obtain 0.36 g of 2-(6-octyloxy-2-naphthyl)-5-butylbenzooxazole (Yield: 56.6%). ##STR190##

Workup

  1. temperatureby refluxing for 310 minutes
  2. extractionextracted from ethyl acetate
  3. customto obtain an organic layer
  4. washThe organic layer was washed with water
  5. dry with materialdried with mirabilite
  6. customdried under reduced pressure
  7. customto obtain a resultant
  8. customThe resultant was recrystallized from ethylacetate
  9. customto obtain a crystal
  10. filtrationThe crystal was filtered
  11. custompurified by silica gel column chromatography (eluent: toluene)
  12. customrecrystallized from acetone

Sources & evidence

ORD record
ord-b2461ebc65244f8f8d1cf4f61ec82c12
Source dataset
uspto-grants-1993_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05244596

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes