Chloride → 4-Hydroxy-4-n-propyl-1-octyne

HRID 1106291Notes

Reaction equation

HRID 1106291 reaction equation
[Mg].[Cl-].[CH3:3][CH2:4][CH2:5][C:6](=[O:11])[CH2:7][CH2:8][CH2:9][CH3:10].[CH2:12](Br)[C:13]#[CH:14].S(=O)(=O)(O)O>CCOCC.C1C=CC=CC=1>[OH:11][C:6]([CH2:12][CH2:13][CH3:14])([CH2:7][CH2:8][CH2:9][CH3:10])[CH2:5][C:4]#[CH:3]

Participants

8

Reactant 5

HCID 312ChlorideHCID 1118Sulfuric AcidHCID 7842Propargyl bromideHCID 11516Octan-4-oneHCID 5462224Magnesium

Product 1

HCID 205539704-Hydroxy-4-n-propyl-1-octyne

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 3283Diethyl EtherSolvent2×

Procedure

14 Grams of powdered (50 mesh) magnesium metal is suspended in 80 ml of ether and activated by addition of 200 mg of mercurie chloride. A solution of 38.4 g of 4-octanone and 36.6 g of propargyl bromide in 120 ml of ether and 50 ml of benzene is added dropwise at a rate which produced a gentle reflux. After the addition is complete, the reaction mixture is stirred for several hours and is then poured into 500 ml of cold 5% sulfuric acid. The organic layer is separated, washed with water twice, dried over sodium sulfate and stripped of solvent. The residue is distilled under vacuum to give the title product.

Workup

  1. customproduced a gentle reflux
  2. additionAfter the addition
  3. customThe organic layer is separated
  4. washwashed with water twice
  5. dry with materialdried over sodium sulfate
  6. distillationThe residue is distilled under vacuum

Sources & evidence

ORD record
ord-3631add237dc47319ce4aa6a8c7e4bdb
Source dataset
uspto-grants-1982_01
Patent number
US04312994

Reaction notes

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