Ammonium Chloride → 4,8-Dimethylnonan-2-ol

HRID 2397295Notes

Reaction equation

HRID 2397295 reaction equation
[CH3:1][Mg]Br.[CH3:4][CH:5]([CH2:7][CH2:8][CH2:9][CH:10]([CH2:12][CH:13]=[O:14])[CH3:11])[CH3:6].[Cl-].[NH4+]>CCOCC>[CH3:11][CH:10]([CH2:9][CH2:8][CH2:7][CH:5]([CH3:4])[CH3:6])[CH2:12][CH:13]([OH:14])[CH3:1]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 1107473,7-DimethyloctanalHCID 178418573HCID 178418573, compound

Product 1

HCID 185101514,8-Dimethylnonan-2-ol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Eighty ml. of a 3M solution of methylmagnesium bromide in ether is added slowly to 31 g. of dihydrocitronellal in 250 ml. of dry ether. The mixture is heated at reflux for about one hour, cooled to 0° and treated with saturated aqueous ammonium chloride until reaction subsides. The organic layer is separated and the aqueous layer extracted with ether. The organic layer and ether extracts are combined, washed with water and brine and dried over magnesium sulfate. Evaporation of the solvent gives 4,8-dimethylnonan-2-ol.

Workup

  1. temperatureThe mixture is heated
  2. temperatureat reflux for about one hour
  3. temperaturecooled to 0°
  4. customThe organic layer is separated
  5. extractionthe aqueous layer extracted with ether
  6. washwashed with water and brine
  7. dry with materialdried over magnesium sulfate
  8. customEvaporation of the solvent

Sources & evidence

ORD record
ord-a51e3828169848f2a9631db0a310434f
Source dataset
uspto-grants-1977_05
Patent number
US04021461

Reaction notes

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