Dicyclohexylcarbodiimide → HCID 178443276, compound

HRID 1086776Notes

Reaction equation

HRID 1086776 reaction equation
[F:1][C:2]1[C:10]([F:11])=[C:9]([O:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH2:25]([C@H:30]1[CH2:35][CH2:34][C@H:33](/[CH:36]=[CH:37]/[CH2:38][O:39][C:40]2[CH:45]=[CH:44][C:43](O)=[CH:42][CH:41]=2)[CH2:32][CH2:31]1)[CH2:26][CH2:27][CH2:28][CH3:29].C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C1C=CN=CC=1.ClCCl>[CH2:25]([C@H:30]1[CH2:31][CH2:32][C@H:33](/[CH:36]=[CH:37]/[CH2:38][O:39][C:40]2[CH:41]=[CH:42][C:43]([O:5][C:4](=[O:6])[C:3]3[CH:7]=[CH:8][C:9]([O:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[C:10]([F:11])[C:2]=3[F:1])=[CH:44][CH:45]=2)[CH2:34][CH2:35]1)[CH2:26][CH2:27][CH2:28][CH3:29]

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 158545222,3-Difluoro-4-dodecyloxybenzoic acidHCID 178444470HCID 178444470, compound

Product 1

HCID 178443276HCID 178443276, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

2.0 g of 2,3-difluoro-4-dodecyloxybenzoic acid, 1.8 g of 4-[(E)-3-(trans-4-pentylcyclohexyl)allyloxy]phenol and 0.1 g of 4-(dimethylamino)pyridine were dissolved in 50 ml of dichloromethane and the solution was treated portionwise within 10 minutes while stirring with 1.4 g of N,N'-dicyclohexylcarbodiimide. The mixture was stirred at room temperature overnight and then filtered. The filtrate was diluted with dichloromethane, washed twice with 50 ml of saturated sodium carbonate solution each time and then with water, dried over magnesium sulphate and concentrated. The crude product obtained was purified by chromatography on silica gel with toluene. The 2,3-difluoro-4-dodecyloxybenzoic acid 4-[(E)-3-(trans-4-pentylcyclohexyl)allyloxy]phenyl ester obtained was recrystallized from ethanol; m.p. (C-SC) 73° C., SC -N 124° C., cl.p. (N-I) 137° C..

Workup

  1. additionthe solution was treated portionwise within 10 minutes
  2. filtrationfiltered
  3. additionThe filtrate was diluted with dichloromethane
  4. washwashed twice with 50 ml of saturated sodium carbonate solution each time
  5. dry with materialwith water, dried over magnesium sulphate
  6. concentrationconcentrated
  7. customThe crude product obtained
  8. customwas purified by chromatography on silica gel with toluene

Sources & evidence

ORD record
ord-f17b67e25c4f454e85a430802795f59f
Source dataset
uspto-grants-1991_07
Patent number
US05032312

Reaction notes

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