Tetrahydrofuran → HCID 11139162, compound

HRID 1525372Notes

Reaction equation

HRID 1525372 reaction equation
[C:1]([OH:14])(=[O:13])/[CH:2]=[CH:3]/[C:4]1[CH:12]=[CH:11][C:9]([OH:10])=[C:6]([O:7][CH3:8])[CH:5]=1.C1C[O:18][CH2:17][CH2:16]1.[H][H]>[Pd].CO>[C:17]([O:10][C:9]1[CH:11]=[CH:12][C:4]([CH2:3][CH2:2][C:1]([OH:14])=[O:13])=[CH:5][C:6]=1[O:7][CH3:8])(=[O:18])[CH3:16]

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 445858Ferulic AcidHCID 178418361HCID 178418361, compound

Product 1

HCID 11139162HCID 11139162, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A 10 g portion of ferulic acid, 150 mL of THF, and 80 mL of methanol were placed in a Parr pressure reactor with 1.5 grams of 10% palladium on charcoal. The reaction mixture was stirred at 30° C. under 60 psi of hydrogen for 12 hours. To remove the palladium on charcoal, the solution was vacuum filtered through celite, dried over magnesium sulfate, and condensed in vacuo. The solid was dissolved in a minimum amount of warm THF and poured into ice chilled hexanes and the solid portion recrystallized from a 5:1 mixture of ethyl acetate and water and dried on the Schlenk line. The crystals of dihydroferulic acid were acetylated by reaction with 9.6 g of acetic anhydride in the presence of 7.6 mL of pyridine. The mixture was stirred at room temperature for three hours and poured over an ice/water slurry (300 mL), to form a white precipitate that was filtered and dried on a Schlenk line, giving a 78% yield.

Workup

  1. customTo remove the palladium on charcoal
  2. filtrationfiltered through celite
  3. dry with materialdried over magnesium sulfate, and condensed in vacuo
  4. dissolutionThe solid was dissolved in a minimum amount of warm THF
  5. additionpoured into ice
  6. temperaturechilled hexanes
  7. customthe solid portion recrystallized from a 5:1 mixture of ethyl acetate and water
  8. customdried on the Schlenk line
  9. customThe crystals of dihydroferulic acid were acetylated by reaction with 9.6 g of acetic anhydride in the presence of 7.6 mL of pyridine
  10. customto form a white precipitate that
  11. filtrationwas filtered
  12. customdried on a Schlenk line
  13. customgiving a 78% yield

Sources & evidence

ORD record
ord-f28e37c1fab04627b9c7dbc21795caca
Source dataset
uspto-grants-2015_07
Patent number
US09080011B2

Reaction notes

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