Methanol → HCID 73453586, compound

HRID 1246587Notes

Reaction equation

HRID 1246587 reaction equation
[H-].[Na+].[NH2:3][C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][CH:5]=1.[CH3:14][C:15](=[CH:17][CH2:18][CH2:19]/[C:20](=[CH:22]/CO)/[CH3:21])[CH3:16].CO>C1(C)C=CC=CC=1>[NH2:3][C:4]1[CH:5]=[CH:6][C:7]([C:8]([O:10][CH2:11][CH:14]=[C:15]([CH3:16])[CH2:17][CH2:18][CH:19]=[C:20]([CH3:22])[CH3:21])=[O:9])=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 12082Methyl 4-aminobenzoateHCID 24758Sodium hydrideHCID 637566Geraniol

Product 1

HCID 73453586HCID 73453586, compoundYield 12.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Sodium hydride (600 mg, cat. 60% disp in oil) was added to a suspension of methyl 4-aminobenzoate (50 g, 330 mmol), geraniol (51 g, 330 mmol) in PhMe (100 mL). The suspension was heated under reflux for 8 hours with the azeotropic removal of MeOH. The mixture was cooled and filtered through a plug of silica (400 mL) with cyclohexane:isopropanol (95:5) as eluant to give the crude ester (X) as a pale yellow oil. Recrystallization from methanol gave the ester (11 g, 12%) as needles.

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
  4. customto give the crude ester (X) as a pale yellow oil
  5. customRecrystallization from methanol

Sources & evidence

ORD record
ord-c7ac3cfa9ac342d18d52b0cba9312ecd
Source dataset
uspto-grants-2006_10
Patent number
US07129204B2

Reaction notes

Loading…