Ammonium Chloride → HCID 54104975, compound

HRID 1414814Notes

Reaction equation

HRID 1414814 reaction equation
C([O:3][C:4](=O)[CH:5]=[C:6]([CH3:14])[CH:7]=[CH:8][CH2:9][C:10]([CH3:13])([CH3:12])[CH3:11])C.[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl-].[NH4+]>C(OCC)C>[CH3:14][C:6]([CH:7]=[CH:8][CH2:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[CH:5][CH2:4][OH:3]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 21226445Aluminium lithium hydrideHCID 54046783HCID 54046783, compound

Product 1

HCID 54104975HCID 54104975, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 4.2 g. of 3,7,7-trimethyl-2,4-octadienoic acid ethyl ester in 90 ml. of absolute diethyl ether is mixed slowly at -20° C. with stirring and under a nitrogen atmosphere with a suspension of 0.75 g. of lithium aluminum hydride in 45 ml. of absolute diethyl ether. The mixture is allowed to attain room temperature in the course of 2 hours and subsequently decomposed in the cold by the dropwise addition of 60 ml. of 10% by weight aqueous ammonium chloride solution. The resulting mass is vacuum filtered over diatomaceous earth and ethereal phase in the filtrate separated. The aqueous phase is extracted with diethyl ether and the combined ether solutions are washed with saturated sodium chloride solution, dried over sodium sulfate and evaporated. There is obtained 3,7,7-trimethyl-2,4-octadien-1-ol which is purified by distillation. Boiling point (bulb-tube distillation) 60° C./0.03 mmHg; nD20 = 1.4790.

Workup

  1. customto attain room temperature in the course of 2 hours
  2. additionsubsequently decomposed in the cold by the dropwise addition of 60 ml
  3. filtrationfiltered over diatomaceous earth and ethereal phase in the filtrate
  4. customseparated
  5. extractionThe aqueous phase is extracted with diethyl ether
  6. washthe combined ether solutions are washed with saturated sodium chloride solution
  7. dry with materialdried over sodium sulfate
  8. customevaporated

Sources & evidence

ORD record
ord-ae39b7313f0f4baca5075803608a159a
Source dataset
uspto-grants-1977_01
Patent number
US04002647

Reaction notes

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