Dicyclohexylcarbodiimide → HCID 178444552, compound

HRID 1285063Notes

Reaction equation

HRID 1285063 reaction equation
[CH:1](/[C@H:6]1[CH2:11][CH2:10][C@H:9]([C:12]([OH:14])=[O:13])[CH2:8][CH2:7]1)=[CH:2]\[CH2:3][CH2:4][CH3:5].[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](/[CH:1]=[CH:2]/[CH2:3][CH2:4][CH3:5])[CH2:11][CH2:10]2)=[O:14])=[CH:20][CH:19]=1)[CH3:16]

Participants

7

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 121504-EthoxyphenolHCID 178444556HCID 178444556, compound

Product 1

HCID 178444552HCID 178444552, compoundYield 83.8%

Reagents, catalysts & solvents 3

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

Procedure

A mixture of 800 mg of trans-4-(trans-1-pentenyl)cyclohexanecarboxylic acid, 675.64 mg of p-ethoxyphenol, 1.01 g of dicyclohexylcarbodiimide and 49.79 mg of 4-(dimethylamino)pyridine was suspended in 14.5 ml of methylene chloride and stirred at room temperature for 20 hours. The mixture was subsequently diluted with diethyl ether, the precipitated urea was filtered off and the filtrate was concentrated. The residue was taken up in hexane and 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 1.080 g (83.8%) of trans-4-(trans-1-pentenyl)cyclohexanecarboxylic acid p-ethoxyphenyl ester. After recrystallization from 40 ml of hexane, there were finally obtained 880 mg of product in the form of transparent crystals; m.p. (C-N) 57.2° C., cl.p. (N-I) 93.1° C.

Workup

  1. filtrationthe precipitated urea was filtered off
  2. concentrationthe filtrate was concentrated
  3. washwashed 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-0345c2d9953449f782e0236bcb693c9b
Source dataset
uspto-grants-1986_01
Patent number
US04565425

Reaction notes

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