Chloride → 4-Benzoyloxy-1-octyne

HRID 1856326Notes

Reaction equation

HRID 1856326 reaction equation
[CH:1]#[C:2][CH2:3][CH:4]([OH:9])[CH2:5][CH2:6][CH2:7][CH3:8].[Cl-].[OH2:11].[CH:12]#[CH:13]>N1C=CC=CC=1>[C:12]([O:9][CH:4]([CH2:5][CH2:6][CH2:7][CH3:8])[CH2:3][C:2]#[CH:1])(=[O:11])[C:13]1[CH:5]=[CH:4][CH:3]=[CH:2][CH:1]=1

Participants

6

Reactant 4

HCID 312ChlorideHCID 962WaterHCID 6326AcetyleneHCID 1036561-Octyn-4-ol

Product 1

HCID 204420544-Benzoyloxy-1-octyne

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a stirred solution of 63. g (0.50 moles) of 1-octyn-4-ol (Example 93) in 500 ml of pyridine is added 77 g (0.55 moles) of beazoyl chloride. After stirring for 1.5 hours the mixture is treated with 10 ml of water, allowed to stand for 15 minutes, and concentrated. A solution of the residue in ether is washed successively with ice-cold hydrochloric acid, water, sodium bicarbonate solution, and brine. The solution is dried over magnesium sulfate, filtered through Celite, and concentrated to give an oil, λ max. 3240 (terminal acetylene) and 1730 cm-1 (benzyloxy group).

Workup

  1. waitto stand for 15 minutes
  2. concentrationconcentrated
  3. washA solution of the residue in ether is washed successively with ice-cold hydrochloric acid, water, sodium bicarbonate solution, and brine
  4. dry with materialThe solution is dried over magnesium sulfate
  5. filtrationfiltered through Celite
  6. concentrationconcentrated
  7. customto give an oil, λ max

Sources & evidence

ORD record
ord-c5a039bbc62643b7bbc6bff5b5abc563
Source dataset
uspto-grants-1980_08
Patent number
US04218566

Reaction notes

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