Dicyclohexylcarbodiimide → HCID 67913761, compound

HRID 846564Notes

Reaction equation

HRID 846564 reaction equation
[C:1]([O:16][C:17]1[CH:25]=[CH:24][C:20]([C:21]([OH:23])=[O:22])=[CH:19][CH:18]=1)(=[O:15])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].O[C:27]1[CH:32]=[CH:31][C:30]([C:33]2[CH:38]=[CH:37][C:36]([C:39](=[O:48])[CH:40]([CH3:47])[CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH3:46])=[CH:35][CH:34]=2)=[CH:29][CH:28]=1.C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C1C=CN=CC=1.ClCCl>[C:1]([O:16][C:17]1[CH:25]=[CH:24][C:20]([C:21]([OH:23])=[O:22])=[CH:19][CH:18]=1)(=[O:15])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].[CH3:47][CH:40]([CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH3:46])[C:39]([C:36]1[CH:37]=[CH:38][C:33]([C:30]2[CH:31]=[CH:32][CH:27]=[CH:28][CH:29]=2)=[CH:34][CH:35]=1)=[O:48]

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 145974864-Hydroxy-4'-(2-methyloctanoyl) biphenylHCID 543778314-(Tetradecanoyloxy)benzoic acid

Product 1

HCID 67913761HCID 67913761, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Into a flask were charged 96.2 mg (0.28 mmol) of 4-tetradecanoyloxy benzoic acid, 78.0 mg (0.25 mmol) of 4-hydroxy-4'-(2-methyloctanoyl) biphenyl, 63.5 mg (0.31 mmol) of dicyclohexylcarbodiimide, 3.5 mg (0.03 mmol) of 4-dimethylamino pyridine and 5 ml of dried dichloromethane, which was heated under reflux for 7 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 further with water, dried on anhydrous magnesium sulfate, and the solvent was distilled off. This product was recrystallized with ethanol to obtain 63.5 mg (yield 40%) of white 4-tetradecanoyloxy benzoic acid-4-(2-methyloctanoyl) biphenyl.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 7 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 and further with water
  6. dry with materialdried on anhydrous magnesium sulfate
  7. distillationthe solvent was distilled off
  8. customThis product was recrystallized with ethanol

Sources & evidence

ORD record
ord-efd367bae7d4482eb88eb33e8d656c24
Source dataset
uspto-grants-1992_08
Patent number
US05137653

Reaction notes

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