HCID 70574310, compound → HCID 9859690, compound

HRID 1389144Notes

Reaction equation

HRID 1389144 reaction equation
[F:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[CH:5]=[C:4]([C:14](O)=[CH:15][C:16](=[O:18])[CH3:17])[CH:3]=1.[H][H]>C(O)(=O)C.[Pd]>[F:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[CH:5]=[C:4]([CH2:14][CH2:15][C:16](=[O:18])[CH3:17])[CH:3]=1

Participants

5

Reactant 2

HCID 70574310HCID 70574310, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 9859690HCID 9859690, compoundYield 49.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

4-(4-Fluoro-6-methoxy-2-naphthyl)-4-hydroxy-but-3-en-2-one (3 g) was hydrogenated at atmospheric pressure and room temperature in glacial acetic acid (150 ml) using 10% palladium on carbon (0.5 g) catalyst. When hydrogen uptake had ceased the catalyst was removed by filtration and the filtrate concentrated. The residue was taken up in ether and the resulting solution washed with sodium bicarbonate solution, then water, dried (MgSO4) and concentrated in vacuo to give a low melting solid which was recrystallised from ether to give colourless crystals (1.40 g) m.p. 69°-70° C. 'H Nmr (CDCl3)δ: 6.81-7.71 (m, 5H), 3.89 (s, 3H), 2.88-2.99 (m, 4H), 2.12 (s, 3H).

Workup

  1. customwas removed by filtration
  2. concentrationthe filtrate concentrated
  3. washthe resulting solution washed with sodium bicarbonate solution
  4. dry with materialwater, dried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customto give a low melting solid which
  7. customwas recrystallised from ether

Sources & evidence

ORD record
ord-0844db7f562c4804aea477238fa02ee9
Source dataset
uspto-grants-1981_01
Patent number
US04243682

Reaction notes

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