Dicyclohexylcarbodiimide → HCID 178442195, compound

HRID 1250131Notes

Reaction equation

HRID 1250131 reaction equation
[CH2:1]([C@H:6]1[CH2:11][CH2:10][C@H:9](/[CH:12]=[CH:13]/[C@H:14]2[CH2:19][CH2:18][C@H:17]([C:20]([OH:22])=[O:21])[CH2:16][CH2:15]2)[CH2:8][CH2:7]1)[CH2:2][CH2:3][CH2:4][CH3:5].[CH2:23]([C:28]1[CH:33]=[CH:32][C:31](O)=[CH:30][CH:29]=1)[CH2:24][CH2:25][CH2:26][CH3:27].C1CCC(N=C=NC2CCCCC2)CC1.C1(C)C=CC=CC=1.CCCCCCC>CN(C1C=CN=CC=1)C.ClCCl>[CH2:1]([C@H:6]1[CH2:11][CH2:10][C@H:9](/[CH:12]=[CH:13]/[C@H:14]2[CH2:15][CH2:16][C@H:17]([C:20]([O:22][C:31]3[CH:30]=[CH:29][C:28]([CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])=[CH:33][CH:32]=3)=[O:21])[CH2:18][CH2:19]2)[CH2:8][CH2:7]1)[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

7

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 269754-PentylphenolHCID 22263336Toluene heptaneHCID 178444464HCID 178444464, compound

Product 1

HCID 178442195HCID 178442195, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

(E)-trans-4-(2-(trans-4-pentylcyclohexyl)vinyl)cyclohexane carboxylic acid in an amount of 1.1 g (3.6 mmol), 0.7 g (4.3 mmol) of 4-pentylphenol, 0.1 g (1.1 mmol) of DMAP, and 20 ml of dichloromethane were mixed. To this mixture was added dropwise 4 ml of solution of 1.0 g (4.7 mmol) of DCC in dichloromethane while being cooled with ice in 5 min, and stirred as it was for 12 hours. Separated crystals were filtered off. To the filtrate was added 70 ml of toluene, washed with 2N-NaOH five times and with water thrice, and then dried over anhydrous magnesium sulfate. The solvent was distilled off under a reduced pressure. The residue thus obtained was subjected to silica gel column chromatography (eluent: toluene/heptane=1/1) to obtain 1.5 g of a crude (E)-4-pentylphenyl trans-4-(2-(trans-4-pentylcyclohexyl)vinyl)cyclohexanecarboxylate. This crude product was recrystallized from a mixed solvent of heptane/diethyl ether to obtain 1.2 g of the subjective compound (yield 74.7%).

Workup

  1. temperaturewhile being cooled with ice in 5 min
  2. customSeparated crystals
  3. filtrationwere filtered off
  4. additionTo the filtrate was added 70 ml of toluene
  5. washwashed with 2N-NaOH five times and with water thrice
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationThe solvent was distilled off under a reduced pressure
  8. customThe residue thus obtained

Sources & evidence

ORD record
ord-f89faf3682f5423ebf15de8fca43eeff
Source dataset
uspto-grants-2002_01
Patent number
US06337034B1

Reaction notes

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