Phenylacetylene → 1-Methoxy-3-(1-octynyl)benzene

HRID 2213964

Reaction equation

HRID 2213964 reaction equation
[CH:1]#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]C.C1(C#C)C=CC=CC=1.[CH3:17][O:18][C:19]1[CH:20]=[C:21]([CH:24]=[CH:25][CH:26]=1)[C:22]#N>C(#N)C1C=CC=CC=1>[CH3:17][O:18][C:19]1[CH:26]=[CH:25][CH:24]=[C:21]([C:22]#[C:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7])[CH:20]=1

Participants

5

Reactant 3

HCID 10821PhenylacetyleneHCID 123701-OctyneHCID 737123-Methoxybenzonitrile

Product 1

HCID 112644061-Methoxy-3-(1-octynyl)benzeneYield 80%

Reagents, catalysts & solvents 1

HCID 7505BenzonitrileSolvent

Procedure

The procedure was identical to Example 1, with the exception that 1-octyne (0.590 ml; 0.441 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 23 h at 65° C. showed the presence of 1.60 mmol (80% yield) of 1-methoxy-3-(1-octynyl)benzene and no remaining 3-methoxybenzonitrile in the reaction mixture.

Sources & evidence

ORD record
ord-5f04e1a58dd1481fba7dc2ea97aa610f
Source dataset
uspto-grants-2006_09
Patent number
US07105707B2

Linked notes

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