Hydrogen Bromide → 1-Bromoundecane

HRID 1381722Notes

Reaction equation

HRID 1381722 reaction equation
[CH2:1](O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11].[BrH:13].S(=O)(=O)(O)O>O>[Br:13][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11]

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 1118Sulfuric AcidHCID 81841-Undecanol

Product 1

HCID 127441-BromoundecaneYield 62.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Undecanol (14 g), 48% aqueous hydrobromic acid (30 g) and concentrated sulphuric acid (5 ml) are heated together under reflux for 51/2 hours. After cooling, water is added and the organic layer is separated, washed with concentrated sulphuric acid (20 ml), brine (50 ml) and dilute aqueous sodium carbonate (50 ml), and is then dried over calcium chloride. Distillaion under vacuum gives 1-bromoundecane (12 g) as a yellow oil, b.p. 60°-70° C./0.1 mm.

Workup

  1. temperatureunder reflux for 51/2 hours
  2. temperatureAfter cooling
  3. customthe organic layer is separated
  4. washwashed with concentrated sulphuric acid (20 ml), brine (50 ml) and dilute aqueous sodium carbonate (50 ml)
  5. dry with materialis then dried over calcium chloride

Sources & evidence

ORD record
ord-b8cf9a4583a548508d7feebf9e012f59
Source dataset
uspto-grants-1989_02
Patent number
US04803289

Reaction notes

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