Methanol → HCID 21904089, compound

HRID 1246589Notes

Reaction equation

HRID 1246589 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.[C:14]1([CH2:20][CH2:21][CH2:22][CH2:23]CO)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[CH3:26]O>C1(C)C=CC=CC=1>[CH3:26][CH:22]([CH2:21][CH2:20][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[CH2:23][CH2:11][O:10][C:8](=[O:9])[C:7]1[CH:6]=[CH:5][C:4]([NH2:3])=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 12082Methyl 4-aminobenzoateHCID 24758Sodium hydrideHCID 615235-Phenyl-1-pentanol

Product 1

HCID 21904089HCID 21904089, compoundYield 25%

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 (30 g, 19 mmol), 3-methyl, 5-phenyl pentanol (36 g, 20 mmol) in PhMe (100 mL). The suspension was heated under reflux for 24 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 ester as a pale yellow oil (15 g, 25%) which slowly crystallized.

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-669d5e08241b45298c70598c556f71cb
Source dataset
uspto-grants-2006_10
Patent number
US07129204B2

Reaction notes

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