Methane → HCID 9795158, compound

HRID 1194472Notes

Reaction equation

HRID 1194472 reaction equation
[OH:1][C:2]1[C:3]([OH:20])=[CH:4][C:5]2[O:10][CH:9]=[C:8]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=3)[C:7](=O)[C:6]=2[CH:19]=1.C>O1CCOCC1.C(O)C.S(=O)(=O)(O)O.[Pd]>[OH:1][C:2]1[C:3]([OH:20])=[CH:4][C:5]2[O:10][CH2:9][CH:8]([C:11]3[CH:12]=[CH:13][C:14]([F:17])=[CH:15][CH:16]=3)[CH2:7][C:6]=2[CH:19]=1

Participants

6

Reactant 2

HCID 297MethaneHCID 21270129HCID 21270129, compound

Product 1

HCID 9795158HCID 9795158, compound

Reagents, catalysts & solvents 3

HCID 1118Sulfuric AcidCatalystHCID 23938PalladiumCatalystHCID 22560076Dioxan ethanolSolvent

Procedure

6,7-Dihydroxy-3-(4-fluorophenyl)-4H-1-benzopyran-4-one (1.2 g), dissolved in a mixture of dioxan/ethanol 4:6 (40 ml), is hydrogenated for 24 h at room temperature over palladium 5% on active charcoal (0.48 g) in the presence of a few drops of conc. sulphuric acid. After filtration of the catalyst, the filtrate is evaporated to dryness under vacuum. An oil is obtained which crystallizes to give 3,4-dihydro-6,7-dihydroxy-3-(4-fluorophenyl)-2H-1-benzopyran, m.p. 135°-137°.

Workup

  1. filtrationAfter filtration of the catalyst
  2. customthe filtrate is evaporated to dryness under vacuum
  3. customAn oil is obtained which
  4. customcrystallizes

Sources & evidence

ORD record
ord-245ce1c9f98c49f99c5c6e7b856183f5
Source dataset
uspto-grants-1989_03
Patent number
US04814346

Reaction notes

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