Oxalic Acid → 4-(4-Pentylbenzoyloxy)-2,3-difluorobenzonitrile

HRID 1198318Notes

Reaction equation

HRID 1198318 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]([C:38]#[N:39])[CH:34]=[CH:33][C:32]=1O.C(O)(=O)C(O)=O>C1(C)C=CC=CC=1>[CH2:16]([C:21]1[CH:22]=[CH:23][C:24]([C:25]([O:27][C:32]2[CH:33]=[CH:34][C:35]([C:38]#[N:39])=[C:36]([F:37])[C:31]=2[F:30])=[O:26])=[CH:28][CH:29]=1)[CH2:17][CH2:18][CH2:19][CH3:20]

Participants

6

Reactant 4

HCID 971Oxalic AcidHCID 10868DicyclohexylcarbodiimideHCID 334794-Pentylbenzoic acidHCID 27369782,3-Difluoro-4-hydroxybenzonitrile

Product 1

HCID 144956274-(4-Pentylbenzoyloxy)-2,3-difluorobenzonitrile

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A mixture of 0.11 mol of dicyclohexylcarbodiimide and 20 ml of toluene is added to a mixture of 0.1 mol of p-pentylbenzoic acid, 0.1 mol of 2,3-difluoro-4-cyanophenol (prepared according to Example 4), 1.5 g of 4-N,N-dimethylaminopyridine and 200 ml of toluene. After the mixture has been stirred at room temperature for 4 hours, 0.4 g of oxalic acid is added and stirring is continued for a further 30 minutes. Customary working up gives 4-(4-pentylbenzoyloxy)-2,3-difluorobenzonitrile, mp. 33° C.

Workup

  1. stirringstirring
  2. waitis continued for a further 30 minutes

Sources & evidence

ORD record
ord-b7ff4a3760e340fb8a48558b10b107fd
Source dataset
uspto-grants-1994_01
Patent number
US05279764

Reaction notes

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