Oxalic Acid → 2,3,4-Trifluorophenyl p-pentylbenzoate

HRID 1198315Notes

Reaction equation

HRID 1198315 reaction equation
C1(N=C=NC2CCCCC2)CCCCC1.[CH2:16]([C:21]1[CH:29]=[CH:28][C:24]([C:25]([OH:27])=[O:26])=[CH:23][CH:22]=1)[CH2:17][CH2:18][CH2:19][CH3:20].[F:30][C:31]1[C:36]([F:37])=[C:35]([F:38])[CH:34]=[CH:33][C:32]=1O.FC1C=CC=C(F)C=1F.C([Li])CCC.O=O.C(O)(=O)C(O)=O>CN(C)C1C=CN=CC=1.C1(C)C=CC=CC=1>[CH2:16]([C:21]1[CH:22]=[CH:23][C:24]([C:25]([O:27][C:34]2[CH:33]=[CH:32][C:31]([F:30])=[C:36]([F:37])[C:35]=2[F:38])=[O:26])=[CH:28][CH:29]=1)[CH2:17][CH2:18][CH2:19][CH3:20]

Participants

10

Reactant 7

HCID 971Oxalic AcidHCID 977OxygenHCID 10868DicyclohexylcarbodiimideHCID 151471,2,3-TrifluorobenzeneHCID 334794-Pentylbenzoic acidHCID 1231742,3,4-TrifluorophenolHCID 178418339Butyllithium

Product 1

HCID 144956512,3,4-Trifluorophenyl p-pentylbenzoate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1140TolueneSolvent2×

Procedure

A mixture of 10 mmol of dicyclohexylcarbodiimide and 1.5 ml of toluene is added to a amixture of 10 mmol of p-pentylbenzoic acid, 10 mmol 2,3,4-trifluorophenol (prepared from 1,2,3-trifluorobenzene in accordance with the literature: A. M. Roe et al., Chem. Comm. 1965, 582, by metalation with n-butyllithium at -50° C. analogously to Example 2 and subsequent oxygenation with atmospheric oxygen), 1 mmol of 4-dimethylaminopyridine and 15.0 ml of toluene. After the mixture has been stirred at room temperature for 4 hours, 20 mg of oxalic acid are added and the mixture is stirred for a further 30 minutes. Customary working up gives 2,3,4-trifluorophenyl p-pentylbenzoate.

Workup

  1. stirringthe mixture is stirred for a further 30 minutes

Sources & evidence

ORD record
ord-0fcd157dfd5544aca69799d7abb317cd
Source dataset
uspto-grants-1994_01
Patent number
US05279764

Reaction notes

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