Pyridine → 4-Benzoyloxy-1-octyne

HRID 2419949Notes

Reaction equation

HRID 2419949 reaction equation
[CH:1]#[C:2][CH2:3][CH:4]([OH:9])[CH2:5][CH2:6][CH2:7][CH3:8].N1C=CC=CC=1.[C:16](Cl)(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C#C>O>[C:16]([O:9][CH:4]([CH2:5][CH2:6][CH2:7][CH3:8])[CH2:3][C:2]#[CH:1])(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 6326AcetyleneHCID 7412Benzoyl chlorideHCID 1036561-Octyn-4-ol

Product 1

HCID 204420544-Benzoyloxy-1-octyne

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred solution of 63. g. (0.50 moles) of 1-octyn-4-ol (Example 87) 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, max. 3240 (terminal acetylene) and 1730 cm-1 (benzoyloxy group).

Workup

  1. additionis treated with 10 ml
  2. waitto stand for 15 minutes
  3. concentrationconcentrated
  4. washA solution of the residue in ether is washed successively with ice-cold hydrochloric acid, water, sodium bicarbonate solution, and brine
  5. dry with materialThe solution is dried over magnesium sulfate
  6. filtrationfiltered through Celite
  7. concentrationconcentrated
  8. customto give an oil, max

Sources & evidence

ORD record
ord-5b19ecd9cd8a4bebad4b9adaf7ddb224
Source dataset
uspto-grants-1978_08
Patent number
US04107441

Reaction notes

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