1,6-Dibromohexane → HCID 19996103, compound

HRID 359751Notes

Reaction equation

HRID 359751 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][CH2:7][CH2:8][OH:9].[Br:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]Br.[OH-].[Na+]>O>[Br:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][O:9][CH2:8][CH2:7][CH2:6][C:2]1[S:1][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 123681,6-DibromohexaneHCID 14798Sodium HydroxideHCID 131098663-(Thiophen-2-yl)propan-1-ol

Product 1

HCID 19996103HCID 19996103, compoundYield 61.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2-thiophenepropanol (5 g), 1,6-dibromohexane (25 g), 50% aqueous sodium hydroxide (25 ml) and TAB (500 mg) was stirred at room temperature overnight. Water (100 ml) was added and the mixture was extracted with ether (2×100 ml). The organic layer was dried and concentrated to an oil which was purified by FCC eluting with hexane to give the title compound as a colourless oil (6.6 g). T.l.c. (hexane-diethyl ether 9:1) Rf 0.50.

Workup

  1. extractionthe mixture was extracted with ether (2×100 ml)
  2. customThe organic layer was dried
  3. concentrationconcentrated to an oil which
  4. customwas purified by FCC
  5. washeluting with hexane

Sources & evidence

ORD record
ord-b3bd14b4d866436b8ba33887ba062bb8
Source dataset
uspto-grants-1991_03
Patent number
US05002966

Reaction notes

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