Umbelliferone → 7-Hydroxychromanone

HRID 345746Notes

Reaction equation

HRID 345746 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8](=[O:12])[O:9]2)=[CH:4][CH:3]=1.CCOC(C)=O.CCCCCC>C(O)C.[Pd]>[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][C:8](=[O:12])[O:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 5281426UmbelliferoneHCID 21226206Ethyl acetate hexane

Product 1

HCID 2981307-Hydroxychromanone

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 7-hydroxycoumarin (5.0 g, 0.031 mol; Aldrich Chemical Company) in absolute ethanol (200 mL) was hydrogenated under pressure in a Parr apparatus over 10% Pd/C (Catalyst; 500 mg, 50% water; Kodak Inc., Rochester, N.Y.) for 24 hours at 55° C. Thin layer chromatography (TLC; Silica gel: EtOAc/hexane: 1:1) showed completion of the reaction. The reaction mixture was then filtered over a bed of Celite (Rohm and Haas Co., Philadelphia, Pa.) and evaporated in vacuo to provide the crude product (4.5 g). A portion (2.5 g) of this material was recrystallized from toluene and dried under vaccuum to provide 7-hydroxydihydrocoumarin. Yield: 1.83 g; melting point 133°-135.5° C.;

Workup

  1. customcompletion of the reaction
  2. filtrationThe reaction mixture was then filtered over a bed of Celite (Rohm and Haas Co., Philadelphia, Pa.)
  3. customevaporated in vacuo
  4. customto provide the crude product (4.5 g)
  5. customA portion (2.5 g) of this material was recrystallized from toluene
  6. customdried under vaccuum

Sources & evidence

ORD record
ord-9b32d0f1bd03423188c11a3d3e61c12a
Source dataset
uspto-grants-1991_10
Patent number
US05059438

Reaction notes

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