Dicyclohexylcarbodiimide → HCID 22153329, compound

HRID 1435562Notes

Reaction equation

HRID 1435562 reaction equation
[CH:1]1[C:6](/[CH:7]=[CH:8]/[C:9]([OH:11])=[O:10])=[CH:5][CH:4]=[C:3]([OH:12])[CH:2]=1.[CH2:13]1[CH2:18]CC(N=C=NC2CCCCC2)C[CH2:14]1>C(O)CC.CN(C1C=CN=CC=1)C.C(OCC)(=O)C>[C:9]([O:11][CH2:14][CH2:13][CH3:18])(=[O:10])/[CH:8]=[CH:7]/[C:6]1[CH:5]=[CH:4][C:3]([OH:12])=[CH:2][CH:1]=1

Participants

6

Reactant 2

HCID 10868DicyclohexylcarbodiimideHCID 637542P-Coumaric Acid

Product 1

HCID 22153329HCID 22153329, compoundYield 71%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 10311-PropanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

Coumaric acid (0.030 mol) is dissolved in 1-propanol (0334 mol) in a 100 ml round bottom flask. DCC (0.033 mol) is added followed by DMAP (0.003 mol). The mixture is stirred at 50° C. for 24 hours, filtered and the propanol removed under reduced vacuum to leave an oily solid which is taken up in ethyl acetate, washed with saturated aqueous NaHCO3 and distilled water, the ethyl acetate layer dried over MgSO4 to leave after removal of the ethyl acetate the desired product as a pale yellow solid in 71% yield.

Workup

  1. filtrationfiltered
  2. customthe propanol removed under reduced vacuum
  3. customto leave an oily solid which
  4. washwashed with saturated aqueous NaHCO3
  5. distillationdistilled water
  6. dry with materialthe ethyl acetate layer dried over MgSO4
  7. customto leave
  8. customafter removal of the ethyl acetate the desired product as a pale yellow solid in 71% yield

Sources & evidence

ORD record
ord-e55e5244fda64dd19e9e6e27925df9bf
Source dataset
uspto-grants-2009_11
Patent number
US07618697B2

Reaction notes

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