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

HRID 848890Notes

Reaction equation

HRID 848890 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][CH:9]([CH2:10][CH2:11][CH2:12][CH3:13])[CH2:8][C:7]#[C:6][CH:1]=[C:2]=[CH2:3]

Participants

5

Reactant 3

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

Product 1

HCID 867375364-Hydroxy-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. (8 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-04565a9c382f411a8bdb085d7bc4a1d9
Source dataset
uspto-grants-1981_10
Patent number
US04297516

Reaction notes

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