Hydrochloric Acid → HCID 19907426, compound

HRID 2371518Notes

Reaction equation

HRID 2371518 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5](I)=[CH:4][CH:3]=1.[CH2:9]([OH:13])[CH2:10][C:11]#[CH:12].Cl>C(N(CC)CC)C.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[OH:13][CH2:9][CH2:10][C:11]#[C:12][C:2]1[CH:7]=[CH:6][C:5]([C:12]#[C:11][CH2:10][CH2:9][OH:13])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 12208p-DiiodobenzeneHCID 135663-Butyn-1-OL

Product 1

HCID 19907426HCID 19907426, compoundYield 95.2%

Reagents, catalysts & solvents 2

HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 8471TriethylamineSolvent

Procedure

First, 16.5 g of p-diiodobenzene and 8.0 g of 3-butyn-1-ol were dissolved in 200 ml of triethylamine, 0.35 g of bis(triphenylphosphine)palladium (II) chloride and 0.19 g of cuprous iodide were added thereto, and the reaction mixture was stirred under nitrogen gas flow at a room temperature for 3 hours. After the reaction was completed, an insoluble matter was filtered off and the filtrate was evaporated under a reduced pressure. To the residue was added a small amount of ethyl acetate, which was then evaporated under a reduced pressure. To the residue was added water, and the mixture was extracted with 100 ml of ethyl acetate. The extract was washed with a saturated sodium chloride aqueous solution and dried over magnesium sulfate. On the other hand the insoluble matter obtained above was acidified with 1N HCl and extracted with 100 ml of ethyl acetate, and the extract was washed with a saturated sodium chloride aqueous solution and dried over magnesium sulfate. This ethyl acetate layer was combined with the ethyl acetate layer obtained above, and the mixture was evaporated under a reduced pressure to obtain 10.2 g of 1,4-bis(4-hydroxy-1-butynyl)benzene as a yellow residue.

Workup

  1. filtrationan insoluble matter was filtered off
  2. customthe filtrate was evaporated under a reduced pressure
  3. additionTo the residue was added a small amount of ethyl acetate, which
  4. customwas then evaporated under a reduced pressure
  5. additionTo the residue was added water
  6. extractionthe mixture was extracted with 100 ml of ethyl acetate
  7. washThe extract was washed with a saturated sodium chloride aqueous solution
  8. dry with materialdried over magnesium sulfate
  9. customOn the other hand the insoluble matter obtained
  10. extractionextracted with 100 ml of ethyl acetate
  11. washthe extract was washed with a saturated sodium chloride aqueous solution
  12. dry with materialdried over magnesium sulfate
  13. customobtained above
  14. customthe mixture was evaporated under a reduced pressure

Sources & evidence

ORD record
ord-5f7a4c7913214416995b7e3bc1dc11d5
Source dataset
uspto-grants-1992_03
Patent number
US05093370

Reaction notes

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