Nitrobenzene → Propiovanillone

HRID 626125Notes

Reaction equation

HRID 626125 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].C([O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[O:16][CH3:17])(=O)CC.[OH-:18].[Na+].[N+]([C:23]1[CH:28]=CC=C[CH:24]=1)([O-])=O>>[OH:9][C:10]1[CH:15]=[CH:14][C:13]([C:24](=[O:18])[CH2:23][CH3:28])=[CH:12][C:11]=1[O:16][CH3:17]

Participants

5

Reactant 4

HCID 7416NitrobenzeneHCID 14798Sodium HydroxideHCID 348502Guaiacol propionateHCID 6451240Aluminum(III) Chloride

Product 1

HCID 15782PropiovanilloneYield 44%

Conditions

Temperature
60 °C

Procedure

Powdered anhydrous aluminum chloride (3.0 g, 22.5 mmol) was dissolved in anhydrous nitrobenzene (10 mL) at 100° C. The solution was cooled and 2-methoxyphenyl propionate (2.0 g, 11.1 mmol) was added rapidly. The reaction mixture was heated at 60° C. for 1.5 h and cooled, 3 N NaOH was added, and the mixture was stirred for 15 min. The suspension was filtered off, washed with water. The filtrate was then washed with CH2Cl2 twice, acidified with 3 N HCl, extracted with CH2Cl2. The extract was dried, concentrated, and purified by column chromatography (petroleum ether/EtOAc=10/1 to 5/1) to give the desired product (874 mg, 44% yield) as a yellow oil.

Workup

  1. temperatureThe solution was cooled
  2. temperaturecooled
  3. filtrationThe suspension was filtered off
  4. washwashed with water
  5. washThe filtrate was then washed with CH2Cl2 twice
  6. extractionextracted with CH2Cl2
  7. customThe extract was dried
  8. concentrationconcentrated
  9. custompurified by column chromatography (petroleum ether/EtOAc=10/1 to 5/1)

Sources & evidence

ORD record
ord-dbfed6db007f4f84b2730d9babdb0700
Source dataset
uspto-grants-2016_04
Patent number
US09309211B2

Reaction notes

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