Cyclododeca-4,8-diene-1-carbaldehyde → 1-(4,8-Cyclododecadienyl)-2-methyl-1-propanol

HRID 1266957Notes

Reaction equation

HRID 1266957 reaction equation
[CH:1]1([CH:13]=[O:14])[CH2:12][CH2:11][CH2:10][CH:9]=[CH:8][CH2:7][CH2:6][CH:5]=[CH:4][CH2:3][CH2:2]1.[CH:15]([Mg]Cl)([CH3:17])[CH3:16]>C1COCC1>[CH:1]1([CH:13]([OH:14])[CH:15]([CH3:17])[CH3:16])[CH2:12][CH2:11][CH2:10][CH:9]=[CH:8][CH2:7][CH2:6][CH:5]=[CH:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 54140259Cyclododeca-4,8-diene-1-carbaldehydeHCID 178418918HCID 178418918, compound

Product 1

HCID 541109191-(4,8-Cyclododecadienyl)-2-methyl-1-propanolYield 65.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4,8-Cyclododecadiene carboxaldehyde (QRM 2185) [14.0 g; 0.072 mol] was dissolved in THF (50 ml), and isopropylmagnesium chloride [36 ml; 2.0 M in Et2O, 0.072 mol] was added dropwise with stirring under N2. The reaction mixture was stirred for 30 minutes, most solvent was removed in vacuo, and the residue quenched with saturated ammonium chloride solution, then partitioned (Et2O/H2O). The organic layer was separated, washed and dried over MgSO4. The solvent was removed in vacuo, and the residue was chromatographed [silica: Et2O 50%, hexane 50%] to give 1-(4,8-cyclododecadienyl)-2-methyl-1-propanol (11.1 g, 65%) as a colourless oil.

Workup

  1. stirringThe reaction mixture was stirred for 30 minutes
  2. custommost solvent was removed in vacuo
  3. customthe residue quenched with saturated ammonium chloride solution
  4. custompartitioned (Et2O/H2O)
  5. customThe organic layer was separated
  6. washwashed
  7. dry with materialdried over MgSO4
  8. customThe solvent was removed in vacuo
  9. customthe residue was chromatographed [silica: Et2O 50%, hexane 50%]

Sources & evidence

ORD record
ord-1a92c369d76f40aab6ce5a48e1ba8d4d
Source dataset
uspto-grants-2003_04
Patent number
US06551988B1

Reaction notes

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