Hydrochloric Acid → 2,8-Dimethyl-5-nonanol

HRID 1033470Notes

Reaction equation

HRID 1033470 reaction equation
[CH3:1][CH:2]([CH2:4][CH2:5][C:6](=[O:12])[CH2:7][CH2:8][CH:9]([CH3:11])[CH3:10])[CH3:3].[CH3:13][CH:14]([CH2:16][CH2:17][CH:18](O)[CH2:19][CH2:20][CH:21]([CH3:23])[CH3:22])[CH3:15].C(OCC)=O.C([Mg]Br)CC(C)C.Cl.[NH2:38][OH:39].[OH-].[K+].Cl>C(O)C.O>[CH3:3][CH:2]([CH2:4][CH2:5][CH:6]([OH:12])[CH2:7][CH2:8][CH:9]([CH3:11])[CH3:10])[CH3:1].[CH3:13][CH:14]([CH2:16][CH2:17][C:18](=[N:38][OH:39])[CH2:19][CH2:20][CH:21]([CH3:23])[CH3:22])[CH3:15]

Participants

11

Reactant 7

HCID 313Hydrochloric AcidHCID 8025Ethyl formateHCID 14797Potassium HydroxideHCID 62421Diisoamyl ketoneHCID 443297Hydroxyamine hydrochlorideHCID 5578512,8-Dimethyl-5-nonanolHCID 178418529HCID 178418529, compound

Product 2

HCID 5578512,8-Dimethyl-5-nonanolHCID 150299992,8-Dimethylnonan-5-one oxime

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent3×

Procedure

To a solution of 5.11 g of 2,8-dimethylnonan-5-one (b.p.: 103°-105° C./19 mmHg, prepared by oxidizing 2,8-dimethylnonan-5-ol with a bleaching powder; 2,8-dimethylnonan-5-ol was prepared by reaction of ethyl formate and isoamylmagnesium bromide) in 20 ml of ethanol were successively added an aqueous solution of 3.47 of hydroxylamine hydrochloride in 6 ml of water and a solution of 4.77 g of potassium hydroxide in 6 ml of water. The mixture was heated under reflux. The reaction mixture was then poured into 150 ml of ice-containing water. The aqueous mixture was made acidic by addition of 2N hydrochloric acid and extracted with benzene. The organic layer was washed with saturated aqueous sodium chloride, dried over anhydrous sodium sulfate, and evaporated under reduced pressure to remove the solvent. There was obtained 5.21 g of 2,8-dimethylnonan-5-one oxime as a pale brown oil, yield: 93.7%.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux
  3. extractionextracted with benzene
  4. washThe organic layer was washed with saturated aqueous sodium chloride
  5. dry with materialdried over anhydrous sodium sulfate
  6. customevaporated under reduced pressure
  7. customto remove the solvent

Sources & evidence

ORD record
ord-cd85ebe6c9c94127b6a30e6e0ae6a368
Source dataset
uspto-grants-1994_05
Patent number
US05310902

Reaction notes

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