Ammonium Chloride → 4-Hydroxy-4-propadienyl-1-octyne

HRID 2059344Notes

Reaction equation

HRID 2059344 reaction equation
[CH2:1]([Mg]Br)[C:2]#[CH:3].[CH2:6]=[C:7]=[CH:8][C:9](=[O:14])[CH2:10][CH2:11][CH2:12][CH3:13].[Cl-].[NH4+]>CCOCC>[OH:14][C:9]([CH:1]=[C:2]=[CH2:3])([CH2:10][CH2:11][CH2:12][CH3:13])[CH2:8][C:7]#[CH:6]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 11194330Octa-1,2-dien-4-oneHCID 178455849HCID 178455849, compound

Product 1

HCID 130391884-Hydroxy-4-propadienyl-1-octyne

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
25 °C

Procedure

To a stirred solution of 125 mmol. of propargylmagnesium bromide in 85 ml. of ether at -20° C. is added a solution of 11.7 g. (95 mmol.) of 1,2-octadien-4-one in 30 ml. of ether during 30 minutes. After the addition, the solution is stirred at 25° C. overnight, cooled to 0° C., and treated dropwise with 18 ml. of saturated ammonium chloride solution. The mixture is filtered, and the filtrate is washed with brine, dried over magnesium sulfate, and concentrated. The product is distilled from anhydrous potassium carbonate to provide the title compound as a colorless liquid, b.p. 84°-87° C. (7 mm.).

Workup

  1. additionAfter the addition
  2. temperaturecooled to 0° C.
  3. additiontreated dropwise with 18 ml
  4. filtrationThe mixture is filtered
  5. washthe filtrate is washed with brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated
  8. distillationThe product is distilled from anhydrous potassium carbonate

Sources & evidence

ORD record
ord-702e0e49f24e4c20a3d9fcbbf675523e
Source dataset
uspto-grants-1982_03
Patent number
US04322546

Reaction notes

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