Phenylacetylene → HCID 1211950, compound

HRID 1452725Notes

Reaction equation

HRID 1452725 reaction equation
[C:1]1([C:7]#[CH:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:9][C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[C:12](I)[CH:11]=1>>[CH3:9][C:10]1[CH:15]=[CH:14][C:13]2[O:16][C:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)=[CH:8][C:12]=2[CH:11]=1

Participants

3

Reactant 2

HCID 10821PhenylacetyleneHCID 6163922-Iodo-4-methylphenol

Product 1

HCID 1211950HCID 1211950, compound

Procedure

The general procedure was used to convert phenylacetylene and 4-methyl-2-iodophenol to the title product. Purification by flash chromatography (hexanes as the eluent) gave the analytically pure product as a white solid (353 mg, 85% yield). 1H NMR (300 MHz, CDCl3) δ 7.81 (d, J=7.16, 2H), 7.41-7.30 (m, 5H), 7.06 (d, J=7.35, 1H), 6.88 (s, 1H), 2.41 (s, 3H). 13C NMR (75 MHz, CDCl3) δ 155.92, 153.29, 132.2, 130.57, 129.27, 128.70, 128.35, 125.49, 124.79, 120.70, 110.61, 101.06, 21.30. Anal. Calcd. for C15H12O: C, 86.51; H, 5.81. Found C, 86.28; H, 5.90. m.p.: 131° C. (lit., 6131-133° C.).

Sources & evidence

ORD record
ord-2121008b365e4cd8a0508254236629c1
Source dataset
uspto-grants-2009_01
Patent number
US07473786B1

Reaction notes

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