Phenylacetylene → HCID 569275, compound

HRID 428814Notes

Reaction equation

HRID 428814 reaction equation
C1(P(C2CCCCC2)C2CCCCC2)CCCCC1.C1(C#C)C=CC=CC=1.[C:28]([O:36][CH:37]([CH2:41][CH:42]=[CH2:43])[CH2:38]C=C)(=[O:35])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>C1(C)C=CC=CC=1>[C:28]([O:36][CH:37]1[CH2:38][CH:43]=[CH:42][CH2:41]1)(=[O:35])[C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Participants

5

Reactant 3

HCID 10821PhenylacetyleneHCID 75806TricyclohexylphosphineHCID 12033330HCID 12033330, compound

Product 1

HCID 569275HCID 569275, compoundYield 69.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

A 100 ml flask was charged with 0.53 g (1.9 mmol) of tricyclohexylphosphine, 0.62 g (1.0 mmol) of di-μ-chlorobis((p-cymene)chlororuthenium), 50 ml of toluene, 0.22 ml (2 mmol) of phenylacetylene and 8.28 g (38.3 mmol) of 1,6-heptadiene-4-yl benzoate and the mixture was stirred at 80° C. for 22 hours in a nitrogen stream. The reaction solution was washed with an aqueous 1% sodium hydroxide solution and saturated brine in this order, followed by drying using magnesium sulfate anhydride. A solvent was distilled and the residue was subjected to vacuum distillation (73-74° C./5 mmHg) to obtain 5.00 g of an object material in a yield of 69.4%.

Workup

  1. washThe reaction solution was washed with an aqueous 1% sodium hydroxide solution and saturated brine in this order
  2. customby drying
  3. distillationA solvent was distilled
  4. distillationthe residue was subjected to vacuum distillation (73-74° C./5 mmHg)

Sources & evidence

ORD record
ord-5008c655e9d142ceb32699321437fbba
Source dataset
uspto-grants-2001_11
Patent number
US06313365B1

Reaction notes

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