Ammonium Chloride → HCID 68484913, compound

HRID 2361565Notes

Reaction equation

HRID 2361565 reaction equation
[CH3:1][Mg]Br.[CH3:4][CH:5]1[CH:10]=[C:9]([CH3:11])[CH2:8][CH2:7][C:6]1([CH:14]=[CH2:15])[CH:12]=[O:13].[NH4+].[Cl-]>>[CH3:4][CH:5]1[CH:10]=[C:9]([CH3:11])[CH2:8][CH2:7][C:6]1([CH:12]([OH:13])[CH3:1])[CH:14]=[CH2:15]

Participants

4

Reactant 3

HCID 25517Ammonium ChlorideHCID 44542715HCID 44542715, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 68484913HCID 68484913, compoundYield 53%

Procedure

To a solution of methylmagnesium bromide (40 mmol, 1 M in THF) was added a solution of 2,4-dimethyl-1-vinylcyclohex-3-enecarbaldehyde (34 mmol) dropwise at 10° C. The mixture was stirred at room temperature for 1 h and was then cooled to 5° C. A sat. solution of NH4Cl was added dropwise and the mixture was extracted with MTBE (3×50 ml). The combined org. phases were washed with water and brine, dried (MgSO4) and concentrated in vacuo. The residue was purified by chromatography to give (2,4-dimethyl-1-vinylcyclohex-3-enyl)ethanol (53% yield).

Workup

  1. temperaturewas then cooled to 5° C
  2. extractionthe mixture was extracted with MTBE (3×50 ml)
  3. washphases were washed with water and brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by chromatography

Sources & evidence

ORD record
ord-dde4d54023274a87a02f5f3d0bb15bbe
Source dataset
uspto-grants-2014_04
Patent number
US08691746B2

Reaction notes

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