Water → 4-Benzoyloxy-1-octyne

HRID 2057818Notes

Reaction equation

HRID 2057818 reaction equation
[CH:1]#[C:2][CH2:3][CH:4]([OH:9])[CH2:5][CH2:6][CH2:7][CH3:8].[C:10](Cl)(=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.O.C#C>N1C=CC=CC=1>[C:10]([O:9][CH:4]([CH2:5][CH2:6][CH2:7][CH3:8])[CH2:3][C:2]#[CH:1])(=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6326AcetyleneHCID 7412Benzoyl chlorideHCID 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 benzoyl 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, λmax. 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, λmax

Sources & evidence

ORD record
ord-528a405481df44a591a3d50cb490445a
Source dataset
uspto-grants-1980_07
Patent number
US04212969

Reaction notes

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