1,6-Dibromohexane → 2-[4-[(6-Bromohexyl)oxy]butoxy]naphthalene

HRID 2372565Notes

Reaction equation

HRID 2372565 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[O:11][CH2:12][CH2:13][CH2:14][CH2:15][OH:16].[Br:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]Br.[OH-].[Na+]>O>[Br:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][O:16][CH2:15][CH2:14][CH2:13][CH2:12][O:11][C:2]1[CH:3]=[CH:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:1]=1

Participants

5

Reactant 3

HCID 123681,6-DibromohexaneHCID 14798Sodium HydroxideHCID 112067001-Butanol, 4-(2-naphthalenyloxy)-

Product 1

HCID 191018312-[4-[(6-Bromohexyl)oxy]butoxy]naphthalene

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4-[(2-naphthalenyl)oxy]butanol (2.4 g), 1,6-dibromohexane (5.3 ml), TAB (1 g) and 50% sodium hydroxide solution (24 ml) was stirred at room temperature for 19 h. The mixture was diluted with water (100 ml) and extracted with ether (2×150 ml). The combined organic fractions were dried and evaporated in vacuo to give an oil. Purification by FCC eluting with hexane followed by hexane-ether (19:1→8:1) gave the title compound as a colourless oil, (2.34 g), t.l.c. (ether-hexane 1:1) Rf 0.85.

Workup

  1. extractionextracted with ether (2×150 ml)
  2. customThe combined organic fractions were dried
  3. customevaporated in vacuo
  4. customto give an oil
  5. customPurification by FCC
  6. washeluting with hexane

Sources & evidence

ORD record
ord-71d990f7f3c943edb9cc753a0d74766d
Source dataset
uspto-grants-1992_03
Patent number
US05099068

Reaction notes

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