Phenylacetylene → 1-(3,3-Dimethyl-1-butyn-1-yl)-3-methoxybenzene

HRID 2213972Notes

Reaction equation

HRID 2213972 reaction equation
[CH3:1][C:2]([CH3:6])([CH3:5])[C:3]#[CH:4].C1(C#C)C=CC=CC=1.[CH3:15][O:16][C:17]1[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=1)C#N>C(#N)C1C=CC=CC=1>[CH3:15][O:16][C:17]1[CH:18]=[CH:19][CH:22]=[C:23]([C:4]#[C:3][C:2]([CH3:6])([CH3:5])[CH3:1])[CH:24]=1

Participants

5

Reactant 3

HCID 10821PhenylacetyleneHCID 135123,3-Dimethyl-1-butyneHCID 737123-Methoxybenzonitrile

Product 1

HCID 114695331-(3,3-Dimethyl-1-butyn-1-yl)-3-methoxybenzeneYield 92.5%

Reagents, catalysts & solvents 1

HCID 7505BenzonitrileSolvent

Procedure

The procedure was identical to Example 1, with the exception that 3,3-dimethyl-1-butyne (0.488 ml; 0.329 g; 4.00 mmol) was used as a substrate instead of phenylacetylene and 3-methoxybenzonitrile (0.245 ml; 0.266 g; 2.00 mmol) was used as a substrate instead of benzonitrile. GC analysis of the organic phase of the hydrolyzed reaction sample after 16 h at 65° C. showed the presence of 1.85 mmol (92% yield) of 1-methoxy-3-(3,3-dimethyl-1-butynyl)benzene and no remaining 3-methoxybenzonitrile in the reaction mixture.

Sources & evidence

ORD record
ord-aef57bd0731b443c84b6528e143b28e3
Source dataset
uspto-grants-2006_09
Patent number
US07105707B2

Reaction notes

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