Dicyclohexylcarbodiimide → HCID 67913779, compound

HRID 846563Notes

Reaction equation

HRID 846563 reaction equation
[C:1]([O:11][C:12]1[CH:20]=[CH:19][C:15]([C:16]([OH:18])=[O:17])=[CH:14][CH:13]=1)(=[O:10])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].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.ClCCl>[C:1]([O:11][C:12]1[CH:20]=[CH:19][C:15]([C:16]([OH:18])=[O:17])=[CH:14][CH:13]=1)(=[O:10])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].[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 35638214-(Nonanoyloxy)benzoic acidHCID 145974864-Hydroxy-4'-(2-methyloctanoyl) biphenyl

Product 1

HCID 67913779HCID 67913779, compoundYield 42.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Into a flask were charged 80.7 mg (0.29 mmol) of 4-nonanoyloxy benzoic acid, 84.2 mg (0.27 mmol) of 4-hydroxy-4'-(2-methyloctanoyl) biphenyl, 63.5 mg (0.31 mmol) of dicyclohexylcarbodiimide, 6.0 mg (0.05 mmol) of 4-dimethylamino pyridine and 5 ml of dried dichloromethane, which was heated under reflux for 6 hours. After the cooling, the resulting solid was filtered off, and washed with dichloromethane. The organic phase was washed with 0.1 normal hydrochloric acid and then water, dried on anhydrous magnesium sulfate, and the solvent was distilled off. This product was purified by a column chromatography and recrystallized with ethanol to obtain 65.3 mg (yield 42%) of white 4-nonanoyloxy benzoic acid-4-(2-methyloctanoyl) biphenyl.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 6 hours
  3. filtrationAfter the cooling, the resulting solid was filtered off
  4. washwashed with dichloromethane
  5. washThe organic phase was washed with 0.1 normal hydrochloric acid
  6. dry with materialwater, dried on anhydrous magnesium sulfate
  7. distillationthe solvent was distilled off
  8. customThis product was purified by a column chromatography
  9. customrecrystallized with ethanol

Sources & evidence

ORD record
ord-48e649b6f7d34acbbd6841c22533ef8a
Source dataset
uspto-grants-1992_08
Patent number
US05137653

Reaction notes

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