Methane → HCID 21270128, compound

HRID 1194470Notes

Reaction equation

HRID 1194470 reaction equation
[OH:1][C:2]1[CH:19]=[CH:18][C:5]2[C:6](=O)[C:7]([C:10]3[CH:15]=[CH:14][CH:13]=[C:12]([CH3:16])[CH:11]=3)=[CH:8][O:9][C:4]=2[C:3]=1[OH:20].C.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(O)C.O1CCOCC1.C(Cl)Cl.[Pd]>[OH:1][C:2]1[CH:19]=[CH:18][C:5]2[CH2:6][CH:7]([C:10]3[CH:15]=[CH:14][CH:13]=[C:12]([CH3:16])[CH:11]=3)[CH2:8][O:9][C:4]=2[C:3]=1[OH:20]

Participants

7

Reactant 3

HCID 297MethaneHCID 521998p-Toluenesulfonic acid monohydrateHCID 21270161HCID 21270161, compound

Product 1

HCID 21270128HCID 21270128, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 6344DichloromethaneSolventHCID 22560076Dioxan ethanolSolvent

Procedure

7,8-Dihydroxy-3-(3-methylphenyl)-4H-1-benzopyran-4-one (100 mg), dissolved in a mixture of ethanol/dioxan 2:1 (75 ml), is hydrogenated for 24 h at room temperature over palladium 10% on active charcoal (50 mg) in the presence of p-toluenesulphonic acid monohydrate (50 mg). After filtration of the catalyst, the filtrate is evaporated under vacuum to a minimum volume, then diluted with water (75 ml) and neutralized to pH 7 by addition of a saturated solution of NaHCO3. An oil is obtained which is extracted with ethyl acetate. The extract is dried over magnsium sulphate and evaporated under vacuum to yield an amorphous solid which is dissolved in methylene chloride and eluted on a silica gel column. After evaporation of the main fraction, one obtains 3,4-dihydro-7,8-dihydroxy-3-(3-methylphenyl)-2H-1-benzopyran, m.p. 95°-96°.

Workup

  1. filtrationAfter filtration of the catalyst
  2. customthe filtrate is evaporated under vacuum to a minimum volume
  3. additiondiluted with water (75 ml)
  4. additionneutralized to pH 7 by addition of a saturated solution of NaHCO3
  5. customAn oil is obtained which
  6. extractionis extracted with ethyl acetate
  7. dry with materialThe extract is dried over magnsium sulphate
  8. customevaporated under vacuum
  9. customto yield an amorphous solid which
  10. washeluted on a silica gel column
  11. customAfter evaporation of the main fraction, one

Sources & evidence

ORD record
ord-83f4e86b5f8e4f4b98ef0f32731d2091
Source dataset
uspto-grants-1989_03
Patent number
US04814346

Reaction notes

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