Dicyclohexylcarbodiimide → HCID 21649526, compound

HRID 846565Notes

Reaction equation

HRID 846565 reaction equation
C(OC(C1C=CC(C(O)=O)=CC=1)=O)CCCCCCC.O[C:22]1[CH:27]=[CH:26][C:25]([C:28]2[CH:33]=[CH:32][C:31]([C:34](=[O:43])[CH:35]([CH3:42])[CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41])=[CH:30][CH:29]=2)=[CH:24][CH:23]=1.C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH3:42][CH:35]([CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41])[C:34]([C:31]1[CH:32]=[CH:33][C:28]([C:25]2[CH:26]=[CH:27][CH:22]=[CH:23][CH:24]=2)=[CH:29][CH:30]=1)=[O:43]

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 145974864-Hydroxy-4'-(2-methyloctanoyl) biphenylHCID 20143990HCID 20143990, compound

Product 1

HCID 21649526HCID 21649526, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To 10 ml of methylene chloride were added 85 mg (0.31 mmol) of 4-octyloxycarbonyl benzoic acid obtained in Example 32, 95 mg (0.31 mmol) of 4-hydroxy-4'-(2-methyloctanoyl) biphenyl and 20 mg of 4-dimethylamino pyridine, which was added with 70 mg (0.32 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 concentrated and isolated by a column chromatography of silica gel to obtain 42 mg (yield 24%) of white (+)-4-(2-methyloctanoyl) biphenyl, 4-octyloxycarbonyl 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. concentrationThe filtrate was concentrated
  6. customisolated by a column chromatography of silica gel

Sources & evidence

ORD record
ord-1d3b3692813a411f80c36559a253cc29
Source dataset
uspto-grants-1992_08
Patent number
US05137653

Reaction notes

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