1,6-Dibromohexane → HCID 19996072, compound

HRID 359752Notes

Reaction equation

HRID 359752 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6](O)[CH3:7].[Br:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]Br.[OH-:17].[Na+]>O>[Br:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][O:17][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 1027821-(Thiophen-2-yl)ethan-1-ol

Product 1

HCID 19996072HCID 19996072, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2-thienylethanol (10.0 g), 1,6-dibromohexane (57.10 g) and TAB (1.3 g) in 40% sodium hydroxide solution (40 ml) was stirred vigorously under nitrogen at room temperature for 5 h. The mixture was diluted with water (400 ml) and extracted with diethyl ether (2×300 ml), dried and evaporated in vacuo to give an oil. Purification by FCC eluting with hexane-ether (100:0→95:5) gave the title compound as a colourless oil (19.28 g), t.l.c. (hexane-ether 9:1) Rf 0.39.

Workup

  1. extractionextracted with diethyl ether (2×300 ml)
  2. customdried
  3. customevaporated in vacuo
  4. customto give an oil
  5. customPurification by FCC
  6. washeluting with hexane-ether (100:0→95:5)

Sources & evidence

ORD record
ord-12da4949b8af49d0bf21986dc3bf9f61
Source dataset
uspto-grants-1991_03
Patent number
US05002966

Reaction notes

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