Phenyl prop-2-ynoate → Trimesic acid, triphenyl ester

HRID 2090081Notes

Reaction equation

HRID 2090081 reaction equation
[C:1]([C:3]([O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:4])#[CH:2]>CN(C=O)C>[C:1]1([C:3]([O:5][C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)=[O:4])[CH:2]=[C:1]([C:3]([O:5][C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)=[O:4])[CH:2]=[C:1]([C:3]([O:5][C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)=[O:4])[CH:2]=1

Participants

3

Reactant 1

HCID 12320093Phenyl prop-2-ynoate

Product 1

HCID 522508Trimesic acid, triphenyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In the reaction, phenyl acetylenecarboxylate 12 is readily obtained by a simple condensation of phenol 11 and propiolic acid 9 using 1,3-dicyclohexylcarbodiimine (DCC), 4-(dimethylamino)pyridine (DMAP), 4-toluenesulfonic acid (TsOH) and Dichloromethane (DCM). Refluxing the obtained phenyl acetylenecarboxylate 12 in DMF for 24 hours under nitrogen yields the cyclotrimerized product of triphenyl benzene-1,3,5-tricarboxylate 13.

Sources & evidence

ORD record
ord-ad5dfb4afe444c5cb4081eaa1ba613f0
Source dataset
uspto-grants-2013_05
Patent number
US08436118B2

Reaction notes

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