Dicyclohexylcarbodiimide → HCID 21649526, compound

HRID 846566Notes

Reaction equation

HRID 846566 reaction equation
C(C1C=CC(C(O)=O)=CC=1)(=O)CCCCCCCC.O[C:21]1[CH:26]=[CH:25][C:24]([C:27]2[CH:32]=[CH:31][C:30]([C:33](=[O:42])[CH:34]([CH3:41])[CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])=[CH:29][CH:28]=2)=[CH:23][CH:22]=1.C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH3:41][CH:34]([CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])[C:33]([C:30]1[CH:31]=[CH:32][C:27]([C:24]2[CH:25]=[CH:26][CH:21]=[CH:22][CH:23]=2)=[CH:28][CH:29]=1)=[O:42]

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 145974864-Hydroxy-4'-(2-methyloctanoyl) biphenylHCID 147168714-Nonanoyl benzoic acid

Product 1

HCID 21649526HCID 21649526, compoundYield 32.9%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To 10 ml of methylene chloride were added 85 mg (0.32 mmol) of 4-nonanoyl benzoic acid obtained in Example 33, 100 mg (0.32 mmol) of (+)-4-hydroxy-4'-(2-methyloctanoyl) biphenyl and 6 mg of 4-dimethylamino pyridine, which was added with 73 mg (0.35 mmol) of N,N'-dicyclohexylcarbodiimide. This mixture was reacted by heating under reflux for 4 hours, and the precipitated solid was filtered off. The filtrate was condensed, isolated by a column chromatography of silica gel and recrystallized with ethyl alcohol to obtain 31 mg (yield 18%) of white 4-(2-methyloctanoyl) biphenyl, 4-nonanoyl benzoic acid ester having the aforementioned physical and chemical properties.

Workup

  1. customThis mixture was reacted
  2. temperatureby heating
  3. temperatureunder reflux for 4 hours
  4. filtrationthe precipitated solid was filtered off
  5. customcondensed
  6. customisolated by a column chromatography of silica gel
  7. customrecrystallized with ethyl alcohol

Sources & evidence

ORD record
ord-1bc41f622ca64cd8a0d05b7ec5ebda40
Source dataset
uspto-grants-1992_08
Patent number
US05137653

Reaction notes

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