Dicyclohexylcarbodiimide → HCID 54140684, compound

HRID 973714Notes

Reaction equation

HRID 973714 reaction equation
C1([C:10]2[C:11]([C:16]3[CH:21]=[CH:20][C:19]([C:22]([OH:24])=[O:23])=[CH:18][CH:17]=3)=[CH:12][CH:13]=[CH:14][CH:15]=2)C=CC(C(O)=O)=CC=1.BrC1C(Br)=C(C2[C:33]([C:38]3[CH:43]=CC=[CH:40][CH:39]=3)=[CH:34][CH:35]=[CH:36][CH:37]=2)C=CC=1.[C:45]([Cu])#N.[OH-].[K+].[CH3:50][C@@H:51]([CH2:55][CH2:56][CH2:57][CH:58]([CH3:60])[CH3:59])[CH2:52][CH2:53][OH:54].C1CCC(N=C=N[CH:70]2[CH2:75][CH2:74][CH2:73][CH2:72][CH2:71]2)CC1.CN1[C:81](=[O:82])CCC1>C(O)COCCO.CN(C1C=CN=CC=1)C.C1(C)C=CC=CC=1>[CH3:43][CH:38]([CH2:33][CH2:34][CH2:35][CH:36]([CH3:37])[CH3:45])[CH2:39][CH2:40][O:24][C:22]([C:19]1[CH:20]=[CH:21][C:16]([C:11]2[CH:10]=[CH:15][C:14]([C:73]3[CH:72]=[CH:71][C:70]([C:81]([O:54][CH2:53][CH2:52][CH:51]([CH3:50])[CH2:55][CH2:56][CH2:57][CH:58]([CH3:60])[CH3:59])=[O:82])=[CH:75][CH:74]=3)=[CH:13][CH:12]=2)=[CH:17][CH:18]=1)=[O:23]

Participants

11

Reactant 7

HCID 10868DicyclohexylcarbodiimideHCID 13387N-methyl-2-pyrrolidoneHCID 14797Potassium HydroxideHCID 69922391-octanol, 3,7-dimethyl-, (s)-HCID 12715082HCID 12715082, compoundHCID 21705264HCID 21705264, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 54140684HCID 54140684, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1140TolueneSolvent2×HCID 8117Diethylene GlycolSolvent

Procedure

25 mmol of 4,4"-terphenyldicarboxylic acid (obtainable by reaction of dibromoterphenyl with CuCN in NMP and hydrolysis of the dinitrile with KOH in diethylene glycol), 7.9 g of (S)-3,7-dimethyloctanol and 0.12 g of DMAP are taken in 40 ml of toluene. A solution of 9.9 g of DCC in 15 ml of toluene is added dropwise at room temperature, with stirring, the mixture is stirred overnight and chromatographed with toluene on silica gel and the product is recrystallized to give 4,4"-bis-(3,7-dimethyloctyloxycarbonyl)-p-terphenyl.

Workup

  1. stirringthe mixture is stirred overnight
  2. customchromatographed with toluene on silica gel
  3. customthe product is recrystallized

Sources & evidence

ORD record
ord-586ead16baab4333ab01123c61c535bf
Source dataset
uspto-grants-1991_11
Patent number
US05064569

Reaction notes

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