Dicyclohexylcarbodiimide → HCID 178443275, compound

HRID 1590520Notes

Reaction equation

HRID 1590520 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][CH2:39][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][CH2:39][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 178444449HCID 178444449, compound

Product 1

HCID 178443275HCID 178443275, compoundYield 64.5%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

1.7 g of 2,3-difluoro-4-dodecyloxybenzoic acid, 1.5 g of 4-[4E-(trans-4-pentylcyclohexyl)-3-butenyl]phenol and 0.1 g of 4-(dimethylamino)pyridine were dissolved in 250 ml of dichloromethane and the solution was treated portionwise within 10 minutes while stirring with 1/2 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 100 ml of water, dried over magnesium sulphate, filtered and then concentrated. Chromatography of the residue on silica gel with toluene and recrystallization from ethanol gave 2 g of 2,3-difluoro-4-dodecyloxybenzoic acid 4-[4E-(trans-4-pentylcyclohexyl)-3-butenyl]phenyl ester with m.p. (C-SC) 51° C., SC -N 115° C. and cl.p. (N-I) 133° 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 100 ml of water, dried over magnesium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customChromatography of the residue on silica gel with toluene and recrystallization from ethanol

Sources & evidence

ORD record
ord-2ea54149cd6d43e7b9a9fb768e3120ae
Source dataset
uspto-grants-1993_04
Patent number
US05204018

Reaction notes

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