Ethanol → HCID 21904092, compound

HRID 1246588Notes

Reaction equation

HRID 1246588 reaction equation
C[O-].[Na+].[NH2:4][C:5]1[CH:15]=[CH:14][C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:7][CH:6]=1.[CH3:16][C:17](=[CH:19][CH2:20][CH2:21][CH:22](CCO)[CH3:23])[CH3:18].CCO>C1CCCCC1>[NH2:4][C:5]1[CH:6]=[CH:7][C:8]([C:9]([O:11][CH2:12][CH2:13][CH:22]([CH3:23])[CH2:21][CH2:20][CH:19]=[C:17]([CH3:18])[CH3:16])=[O:10])=[CH:14][CH:15]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 2337BenzocaineHCID 8842CitronellolHCID 10942334Sodium Methoxide

Product 1

HCID 21904092HCID 21904092, compoundYield 30.3%

Reagents, catalysts & solvents 1

HCID 8078CyclohexaneSolvent

Procedure

Sodium methoxide (2.5 g, cat.) was added to a suspension of ethyl 4-aminobenzoate (10 g, 60 mmol), citronellol (15 g, 90 mmol) in cyclohexane (100 mL). The suspension was heated under reflux for 8 hours with the azeotropic removal of EtOH. The mixture was cooled and filtered through a plug of silica (400 mL) with cyclohexane:isopropanol (95:5) as eluant to give the ester (5.0 g, 30%)as a pale yellow solid.

Workup

  1. temperatureThe suspension was heated
  2. temperatureThe mixture was cooled
  3. filtrationfiltered through a plug of silica (400 mL) with cyclohexane:isopropanol (95:5) as eluant

Sources & evidence

ORD record
ord-63c17e6a327d4c96bac78833a1ffddea
Source dataset
uspto-grants-2006_10
Patent number
US07129204B2

Reaction notes

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