Hydrogen Bromide → Undecane hydrobromide

HRID 1262928Notes

Reaction equation

HRID 1262928 reaction equation
[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11].[BrH:12]>C(O)(=O)C>[BrH:12].[CH3:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1]

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 14257Undecane

Product 1

HCID 20456496Undecane hydrobromide

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

D,L-2-aza-2'-hydroxy-5,6-benzotricyclo-[6.3.01,8.04,11 ]undecane (2.68 g; 11.7 mmoles) is refluxed under argon in a mixture of acetic acid (67 ml) and 47% hydrobromic acid (677 ml) for 50 hours. The mixture is evaporated to dryness. The residue is dissolved in hot methanol and evaporated onto 15 g silica gel which is then placed on top of 80 g silica gel. Elution with chloroform:methanol:ammonium hydroxide (100:15:1 v:v:v) yields D,L-2-aza-2'-hydroxy-5,6-benzotricyclo[6.3.01,8.04,11 ] undecane hydrobromide: 2.23 g; 89%; melting point: 284°-286° C.

Workup

  1. customThe mixture is evaporated to dryness
  2. dissolutionThe residue is dissolved in hot methanol
  3. customevaporated onto 15 g silica gel which
  4. washElution with chloroform:methanol:ammonium hydroxide (100:15:1 v:v:v)

Sources & evidence

ORD record
ord-fae5a3670c3d46b3a3d88a81a89b004a
Source dataset
uspto-grants-1984_06
Patent number
US04454325

Reaction notes

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