Hydrochloric Acid → Dihydroferulic Acid

HRID 1525373Notes

Reaction equation

HRID 1525373 reaction equation
C([O:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][C:13]([OH:15])=[O:14])=[CH:7][C:6]=1[O:16][CH3:17])(=O)C.[OH-].[Na+].Cl>O>[OH:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][C:13]([OH:15])=[O:14])=[CH:7][C:6]=1[O:16][CH3:17]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 11139162HCID 11139162, compound

Product 1

HCID 14340Dihydroferulic AcidYield 83%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution was prepared from 8.0 g (0.034 mol) of acetyldihydroferulic acid and 4.7 g (0.118 mol) of sodium hydroxide in 100 mL of water and refluxed for 5 h. After cooling to room temperature, the aqueous solution was acidified with hydrochloric acid and extracted with dichloromethane. The organic layer was washed with brine and dried over magnesium sulfate. The evaporation of the solvent left a yellow crude product that was dissolved in dichloromethane and precipitated in hexanes to yield 5.5 g of an off-white powder in 83% yield.

Workup

  1. temperaturerefluxed for 5 h
  2. extractionextracted with dichloromethane
  3. washThe organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customThe evaporation of the solvent
  6. waitleft a yellow crude product that
  7. dissolutionwas dissolved in dichloromethane
  8. customprecipitated in hexanes

Sources & evidence

ORD record
ord-84f93e2ffd0041cfbe54f1c11bacda3f
Source dataset
uspto-grants-2015_07
Patent number
US09080011B2

Reaction notes

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