Sodium Hydroxide → 1-Butanol, 4-(2-naphthalenyloxy)-

HRID 2372564Notes

Reaction equation

HRID 2372564 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=1.C([O-])(=[O:19])C.[Na+].[Cl-].C([N+](CCCCCCCC)(CCCCCCCC)CCC)CCCCCCC.[OH-].[Na+]>CCOCC.C(O)C.O>[CH:8]1[C:9]2[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:15]=[CH:16][C:7]=1[O:6][CH2:5][CH2:4][CH2:3][CH2:2][OH:19]

Participants

8

Reactant 4

HCID 14798Sodium HydroxideHCID 517045Sodium AcetateHCID 27351551-Octanaminium, N,N-dioctyl-N-propyl-, chloride (1:1)HCID 41306352-(4-bromobutoxy)naphthalene

Product 1

HCID 112067001-Butanol, 4-(2-naphthalenyloxy)-Yield 31.9%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 2-[(4-bromobutyl)oxy]naphthalene (5.5 g), sodium acetate (13.1 g), trioctylpropylammonium chloride (1.21 g) and water (19 ml) was stirred at ca 100° for 2 h. 2N sodium hydroxide solution (32 ml) and ethanol (32 ml) were added to the cooled mixture which was stirred for a further 10 min at room temperature. The ethanol was evaporated in vacuo and the residue diluted with brine (150 ml) and extracted with ether (2×100 ml), which was dried and evaporated in vacuo to give a white solid. The solid was dissolved in ether and purified by FCC eluting with hexane-ether (2:1→1:2) to give the title compound as a white solid (1.36 g), m.p. 66.5°-67.5°.

Workup

  1. stirringwas stirred for a further 10 min at room temperature
  2. customThe ethanol was evaporated in vacuo
  3. additionthe residue diluted with brine (150 ml)
  4. extractionextracted with ether (2×100 ml), which
  5. customwas dried
  6. customevaporated in vacuo
  7. customto give a white solid
  8. custompurified by FCC
  9. washeluting with hexane-ether (2:1→1:2)

Sources & evidence

ORD record
ord-08966fa451f94f4fb0b767dae42e493d
Source dataset
uspto-grants-1992_03
Patent number
US05099068

Reaction notes

Loading…