Dicyclohexylcarbodiimide → 4'-Ethylbiphenyl-4-yl 1-cyano-3-methylcyclohexanecarboxylate

HRID 1646475Notes

Reaction equation

HRID 1646475 reaction equation
C1(N=C=NC2CCCCC2)CCCCC1.[C:16]([C:18]1([C:25]([OH:27])=[O:26])[CH2:23][CH2:22][CH2:21][CH:20]([CH3:24])[CH2:19]1)#[N:17].[CH2:28]([C:34]1[CH:39]=[CH:38][C:37]([C:40]2[CH:45]=[CH:44][C:43](O)=[CH:42][CH:41]=2)=[CH:36][CH:35]=1)[CH2:29]CCCC.C(N(CC)C1C=CN=CC=1)C>C(Cl)Cl>[C:16]([C:18]1([C:25]([O:27][C:43]2[CH:44]=[CH:45][C:40]([C:37]3[CH:36]=[CH:35][C:34]([CH2:28][CH3:29])=[CH:39][CH:38]=3)=[CH:41][CH:42]=2)=[O:26])[CH2:23][CH2:22][CH2:21][CH:20]([CH3:24])[CH2:19]1)#[N:17]

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 117687514-DiethylaminopyridineHCID 135748604'-Hexyl-biphenyl-4-olHCID 198007731-Cyano-3-methylcyclohexane-1-carboxylic acid

Product 1

HCID 198007934'-Ethylbiphenyl-4-yl 1-cyano-3-methylcyclohexanecarboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 23 g of dicyclohexylcarbodiimide in 50 ml of CH2Cl2 is added to a mixture of 16 g of 1-cyano-3-methyl-cyclohexanecarboxylic acid, 25 g of 4'-hexyl-biphenyl-4-ol, 1.2 g of 4-diethylaminopyridine and 200 ml of methylene chloride at room temperature and the mixture is stirred for 2 hours. Customary working up and separation by column chromatography (silica gel/toluene) gives 4'-hexylbiphenyl-4-yl 1-cyano-3-methylcyclohexanecarboxylic as the pure product by recrystallization, m.p. 51°, [α]D20 =+2.2°.

Workup

  1. customseparation by column chromatography (silica gel/toluene)
  2. customgives 4'-hexylbiphenyl-4-yl 1-cyano-3-methylcyclohexanecarboxylic as the pure product
  3. customby recrystallization, m.p. 51°, [α]D20 =+2.2°

Sources & evidence

ORD record
ord-80bb676d32b24c96a795b25ed6583c1c
Source dataset
uspto-grants-1993_01
Patent number
US05180521

Reaction notes

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