1-Bromohexane → 1-Undecen-5-ol

HRID 1105508Notes

Reaction equation

HRID 1105508 reaction equation
[CH:1](=[O:6])[CH2:2][CH2:3][CH:4]=[CH2:5].[Mg].Br[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]>CCOCC>[CH2:5]=[CH:4][CH2:3][CH2:2][CH:1]([OH:6])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]

Participants

5

Reactant 3

HCID 81011-BromohexaneHCID 164184-PentenalHCID 5462224Magnesium

Product 1

HCID 104422311-Undecen-5-olYield 88.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

4-pentenal (8.4 g., 0.1 mol) was added dropwise to the Grignard reagent from magnesium turnings (2.88 g., 0.12 mol) and 1-bromohexane (19.8 g., 0.12 mol) in ether (120 ml). The reaction mixture was then refluxed for 2 hours cooled, and quenched with ammonium chloride solution. After layers were separated, ether solution was evaporated and the residue distilled to give 1-undecen-5-ol (15.0 g., 88% yield, b.p. 93°-96°/1.2 torr).

Workup

  1. temperatureThe reaction mixture was then refluxed for 2 hours
  2. temperaturecooled
  3. customquenched with ammonium chloride solution
  4. customAfter layers were separated
  5. customether solution was evaporated
  6. distillationthe residue distilled

Sources & evidence

ORD record
ord-d761e077becb46ef8236c5a10b37369a
Source dataset
uspto-grants-1982_01
Patent number
US04309352

Reaction notes

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