Urea → 4-p-Tolylethynylphenyl 4-vinylcyclohexanecarboxylate

HRID 565157Notes

Reaction equation

HRID 565157 reaction equation
[CH:1]([CH:3]1[CH2:8][CH2:7][CH:6]([C:9]([OH:11])=[O:10])[CH2:5][CH2:4]1)=[CH2:2].[C:12]1([CH3:27])[CH:17]=[CH:16][C:15]([C:18]#[C:19][C:20]2[CH:25]=[CH:24][C:23](O)=[CH:22][CH:21]=2)=[CH:14][CH:13]=1.C1CCC(N=C=NC2CCCCC2)CC1.NC(N)=O>CN(C)C1C=CN=CC=1.C1(C)C=CC=CC=1>[CH:1]([CH:3]1[CH2:8][CH2:7][CH:6]([C:9]([O:11][C:23]2[CH:24]=[CH:25][C:20]([C:19]#[C:18][C:15]3[CH:16]=[CH:17][C:12]([CH3:27])=[CH:13][CH:14]=3)=[CH:21][CH:22]=2)=[O:10])[CH2:5][CH2:4]1)=[CH2:2]

Participants

7

Reactant 4

HCID 1176UreaHCID 10868DicyclohexylcarbodiimideHCID 185381694-Ethenylcyclohexane-1-carboxylic acidHCID 187390274-[2-(4-Methylphenyl)ethynyl]phenol

Product 1

HCID 599291384-p-Tolylethynylphenyl 4-vinylcyclohexanecarboxylate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1140TolueneSolvent2×

Procedure

5.0 g of 4-vinylcyclohexanecarboxylic acid, 6.7 g of 4-p-tolylethynylphenol, 4.0 g of 4-(dimethylamino)pyridine and 250 ml of toluene were mixed at RT, 7.3 g of DCC in 50 ml of toluene were added, and the mixture was stirred vigorously overnight at RT, during which the urea formed precipitated. 1 g of oxalic acid was then added, and the mixture was stirred at RT for a further hour in order to destroy the excess DCC. The conventional work-up gave 4-p-tolylethynylphenyl 4-vinylcyclohexanecarboxylate in the form of colorless crystals.

Workup

  1. customformed
  2. customprecipitated
  3. addition1 g of oxalic acid was then added
  4. customto destroy the excess DCC

Sources & evidence

ORD record
ord-9c62461c638c4c36b920de2febc79126
Source dataset
uspto-grants-2001_01
Patent number
US06171664B2

Reaction notes

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