Pyridine → 4-Benzoyloxy-1-octyne

HRID 1439115Notes

Reaction equation

HRID 1439115 reaction equation
[OH:1][CH:2]([CH2:6][CH2:7][CH2:8][CH3:9])[CH2:3][C:4]#[CH:5].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:1][CH:2]([CH2:6][CH2:7][CH2:8][CH3:9])[CH2:3][C:4]#[CH:5])(=[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 4-hydroxy-1-octyne (Example 893) 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, ν 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, ν max

Sources & evidence

ORD record
ord-c1ff0bb9a3ca47b69d5ca1bf8e479ff2
Source dataset
uspto-grants-1977_11
Patent number
USRE029469

Reaction notes

Loading…