4-Methyl-7-diethylaminocoumarin → Dihydrocoumarin

HRID 2393230

Reaction equation

HRID 2393230 reaction equation
CCN([C:6]1[CH:11]=[CH:10][C:9]2[C:12](C)=[CH:13][C:14]([O:16][C:8]=2[CH:7]=1)=[O:15])CC>C(OCC)(=O)C.[Pd]>[O:16]1[C:8]2[C:9](=[CH:10][CH:11]=[CH:6][CH:7]=2)[CH2:12][CH2:13][C:14]1=[O:15]

Participants

4

Reactant 1

HCID 70504-Methyl-7-diethylaminocoumarin

Product 1

HCID 660DihydrocoumarinYield 156.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of coumarin-1 (11.0 g, 47.5 mmol) in ethyl acetate (150 mL) was treated with 10% Pd/C (100 mg) in a parr bottle. The suspension was then hydrogenated at 80 psi and 80° C. for 6 hours. The suspension was filtered through a bed of celite to remove the Pd/C, and the celite bed washed with warm ethyl acetate (100 mL). The filtrate was concentrated and dried under vacuo to yield 11.0 g (100%) of the 3,4-dihydrocoumarin (2) as an oil;

Workup

  1. filtrationThe suspension was filtered through a bed of celite
  2. customto remove the Pd/C
  3. washthe celite bed washed with warm ethyl acetate (100 mL)
  4. concentrationThe filtrate was concentrated
  5. customdried under vacuo

Sources & evidence

ORD record
ord-85d89f696b114b0283969412a6d3f60b
Source dataset
uspto-grants-1998_09
Patent number
US05807675

Linked notes

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