N,N,N',N'-Tetramethylethylenediamine → Phenylpropiolic Acid

HRID 2410651Notes

Reaction equation

HRID 2410651 reaction equation
CN(C)CCN(C)C.[C:9]([O-:12])([O-])=[O:10].[K+].[K+].[C:15]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)#[CH:16]>Cl[Cu]>[C:17]1([C:15]#[C:16][C:9]([OH:12])=[O:10])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 8037N,N,N',N'-TetramethylethylenediamineHCID 10821PhenylacetyleneHCID 11430Potassium Carbonate

Product 1

HCID 69475Phenylpropiolic Acid

Reagents, catalysts & solvents 1

HCID 62652Cuprous chlorideCatalyst

Procedure

An initial experiment was conducted by using 2 mol % of CuCl, 2 mol % of TMEDA (N,N,N′,N′-tetramethylethylenediamine) ligand, and K2CO3 as base for the carboxylation of 1-ethynylbenzene at ambient temperature and atmospheric pressure. Remarkably, phenylpropiolic acid was produced in excellent yield after acid workup. The isolated pure product was characterized by NMR and elemental analysis. Phenylpropiolic acid was further converted into its methylester and characterized by NMR and GC/MS.

Workup

  1. customat ambient temperature

Sources & evidence

ORD record
ord-810867d5cbcc4f2ebc36a74f568ffc24
Source dataset
uspto-grants-2014_08
Patent number
US08816127B2

Reaction notes

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