Methanol → HCID 20209877, compound

HRID 1246585Notes

Reaction equation

HRID 1246585 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1.[CH3:12][CH:13]([CH2:15][CH2:16][CH2:17][CH:18]([CH2:20]CO)[CH3:19])[CH3:14].CO>C1(C)C=CC=CC=1>[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([O:8][CH2:9][CH2:12][CH:13]([CH3:14])[CH2:15][CH2:16][CH2:17][CH:18]([CH3:20])[CH3:19])=[O:7])=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 77923,7-Dimethyl-1-octanolHCID 12082Methyl 4-aminobenzoate

Product 1

HCID 20209877HCID 20209877, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Na metal (200 mg, cat.) was added to a suspension of methyl 4-aminobenzoate (45 g, 300 mmol), tetrahydrogeraniol (48 g, 300 mmol) in PhMe (250 mL). The suspension was heated under reflux for 3 hours with the azeotropic removal of MeOH. The mixture was cooled and filtered through a plug of silica (400 mL) with cyclohexane: EtOAc (9:1) as eluant to give the ester (24 g, 30%) as a pale yellow oil.

Workup

  1. temperatureThe suspension was heated
  2. temperatureThe mixture was cooled
  3. filtrationfiltered through a plug of silica (400 mL) with cyclohexane: EtOAc (9:1) as eluant

Sources & evidence

ORD record
ord-cc251365f6c74d87af5382079d7c1c38
Source dataset
uspto-grants-2006_10
Patent number
US07129204B2

Reaction notes

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