Dicyclohexylcarbodiimide → HCID 178444551, compound

HRID 247694

Reaction equation

HRID 247694 reaction equation
[CH2:1]([C@H:6]1[CH2:11][CH2:10][C@H:9]([C:12]([OH:14])=[O:13])[CH2:8][CH2:7]1)[CH2:2][CH2:3][CH:4]=[CH2:5].[CH2:15]([O:17][C:18]1[CH:23]=[CH:22][C:21](O)=[CH:20][CH:19]=1)[CH3:16].C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C1C=CN=CC=1.C(Cl)Cl.C(OCC)C>[CH2:15]([O:17][C:18]1[CH:23]=[CH:22][C:21]([O:13][C:12]([C@H:9]2[CH2:8][CH2:7][C@H:6]([CH2:1][CH2:2][CH2:3][CH:4]=[CH2:5])[CH2:11][CH2:10]2)=[O:14])=[CH:20][CH:19]=1)[CH3:16]

Participants

7

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 121504-EthoxyphenolHCID 178444555HCID 178444555, compound

Product 1

HCID 178444551HCID 178444551, compoundYield 83.5%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 520 mg of trans-4-(4-pentenyl)cyclohexanecarboxylic acid, 439.4 mg of p-ethoxyphenol, 765.5 mg of dicyclohexylcarbodiimide and 45 mg of 4-(dimethylamino)pyridine were dissolved in 80 ml of methylene chloride and the solution was stirred at room temperature for 20 hours. Subsequently, the reaction mixture was diluted with diethyl ether, the precipitated urea was filtered off and the filtrate was concentrated. The residue was taken up in hexane and the solution was washed with dilute hydrochloric acid, sodium hydrogen carbonate solution and water. The aqueous phases were back-extracted twice with hexane. The organic phases were dried over magnesium sulphate and evaporated. Low-pressure chromatography of the resulting residue on silica gel with ethyl acetate/petroleum ether (vol. 3:97) gave an 0.7 g (83%) of trans-4-(4-pentenyl)cyclohexanecarboxylic acid p-ethoxyphenyl ester. After recrystallization from 3 ml of methanol there were finally obtained 455 mg of product in the form of colourless crystals; m.p. (C-N) 32.7° C., cl.p. (N-I) 57.5° C.

Workup

  1. filtrationthe precipitated urea was filtered off
  2. concentrationthe filtrate was concentrated
  3. washthe solution was washed with dilute hydrochloric acid, sodium hydrogen carbonate solution and water
  4. extractionThe aqueous phases were back-extracted twice with hexane
  5. dry with materialThe organic phases were dried over magnesium sulphate
  6. customevaporated

Sources & evidence

ORD record
ord-88d42fa00ec645d7b222c81884225647
Source dataset
uspto-grants-1987_11
Patent number
US04709030

Linked notes

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