Carbon Tetrachloride → Benzene, (chloroethynyl)-

HRID 846918Notes

Reaction equation

HRID 846918 reaction equation
[C:1]1([C:7]#[CH:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[Cs+].[Cs+].C(Cl)(Cl)(Cl)[Cl:16]>O.[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC>[Cl:16][C:8]#[C:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 5943Carbon TetrachlorideHCID 10796Cesium carbonateHCID 10821Phenylacetylene

Product 1

HCID 137029Benzene, (chloroethynyl)-Yield 96%

Reagents, catalysts & solvents 1

HCID 16212273Tetrabutylammonium chloride hydrateCatalyst

Procedure

Phenylacetylene (1.02 g, 10 mmol), 1.92 g of cesium carbonate (10 mmol), and 0.15 g tetra-n-butylammonium chloride hydrate and 5 mL carbon tetrachloride were mixed at 70° C. for 5 h. Gas chromatographic analysis of the mixture showed that it contained 1.32 g of 1-chloro-2-phenylacetylene (96% yield).

Sources & evidence

ORD record
ord-04ecc959d6cb4558aa382c57ff38abfc
Source dataset
uspto-grants-1992_08
Patent number
US05138107

Reaction notes

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