1,6-Dibromohexane → 6-[(6-Bromohexyl)oxy]-1-hexyne

HRID 982397Notes

Reaction equation

HRID 982397 reaction equation
[CH2:1]([OH:7])[CH2:2][CH2:3][CH2:4][C:5]#[CH:6].Br[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][Br:15].[OH-].[Na+]>O>[Br:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][O:7][CH2:1][CH2:2][CH2:3][CH2:4][C:5]#[CH:6]

Participants

5

Reactant 3

HCID 123681,6-DibromohexaneHCID 14798Sodium HydroxideHCID 702345-Hexyn-1-ol

Product 1

HCID 218671586-[(6-Bromohexyl)oxy]-1-hexyne

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 5-hexyn-1-ol (5 g), 1,6-dibromohexane (37.29 g), TAB (1 g) and 50% sodium hydroxide solution (20 ml) was stirred under nitrogen for 22 h. The mixture was diluted with water (100 ml) and extracted with diethyl ether (2×150 ml). The combined organic extracts were dried and evaporated in vacuo to give an oil. Purification by FCC eluting with hexane followed by hexane:ether (95:5) gave the title compound as a colourless oil. (7.7 g), t.l.c. (hexane:ether 2:1) Rf 0.80.

Workup

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

Sources & evidence

ORD record
ord-59c0df293c814e9a9d091afec37c2a7c
Source dataset
uspto-grants-1991_02
Patent number
US04996218

Reaction notes

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