Methane → HCID 15628203, compound

HRID 1194471Notes

Reaction equation

HRID 1194471 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][CH:14]=[C:13]([CH3:17])[CH:12]=3)[C:7](=O)[C:6]=2[CH:19]=1.C>O1CCOCC1.C(O)C.S(=O)(=O)(O)O.C(Cl)Cl.[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:16]=[CH:15][CH:14]=[C:13]([CH3:17])[CH:12]=3)[CH2:7][C:6]=2[CH:19]=1

Participants

7

Reactant 2

HCID 297MethaneHCID 21270166HCID 21270166, compound

Product 1

HCID 15628203HCID 15628203, compound

Reagents, catalysts & solvents 4

HCID 1118Sulfuric AcidCatalystHCID 23938PalladiumCatalystHCID 6344DichloromethaneSolventHCID 22560076Dioxan ethanolSolvent

Procedure

6,7-Dihydroxy-3-(3-methylphenyl)-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 concentrated sulphuric acid. After filtration of the catalyst, the filtrate is evaporated to dryness under vacuum. An oil is obtained which is dissolved in methylene chloride. The solution is washed with water and dried over magnesium sulphate to give an oil which on crystallization yields 3,4-dihydro-6,7-dihydroxy-3-(3-methylphenyl)-2H-1-benzopyran, m.p. 146°-148°.

Workup

  1. filtrationAfter filtration of the catalyst
  2. customthe filtrate is evaporated to dryness under vacuum
  3. customAn oil is obtained which
  4. washThe solution is washed with water
  5. dry with materialdried over magnesium sulphate
  6. customto give an oil which
  7. customon crystallization

Sources & evidence

ORD record
ord-47b16d3373dc4259afde6bd11eaaef07
Source dataset
uspto-grants-1989_03
Patent number
US04814346

Reaction notes

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