Carbon Tetrachloride → Benzene, (chloroethynyl)-

HRID 654605Notes

Reaction equation

[C:1]1([C:7]#[CH:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[K+].[K+].O.O.O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Cl:36]C(Cl)(Cl)Cl>>[Cl:36][C:8]#[C:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

Reactant 4

HCID 5943Carbon Tetrachloride

HCID 10821Phenylacetylene

HCID 11430Potassium Carbonate

HCID 11726816Tetrabutylammonium Fluoride Trihydrate

Product 1

HCID 137029Benzene, (chloroethynyl)-Yield 99%

Conditions

Temperature: 24 °C

Procedure

In a 10 mL round-bottom flask, a mixture of 0.51 g phenylacetylene (5 mmol), 0.7 g potassium carbonate (5 mmol), 165 mg tetra-n-butylammonium fluoride trihydrate, and 3 mL tetrachloromethane was stirred at 24° C. for 10 min. After filtration of the solids, the filtrate was found to contain 0.68 g of 1-chloro-2-phenylacetylene (99% yield).

Workup

filtrationAfter filtration of the solids

Sources & evidence

ORD record: ord-ce4b577c2cc64cd9a7e219a71838cc0a
Source dataset: uspto-grants-1992_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05132475

Reaction notes

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