Methane → HCID 21270140, compound

HRID 1194466Notes

Reaction equation

HRID 1194466 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][C:13]([CH3:16])=[CH:12][CH:11]=3)=[CH:8][O:9][C:4]=2[C:3]=1[CH3:20].C.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>O1CCOCC1.C(O)C.[Pd]>[OH:1][C:2]1[CH:19]=[CH:18][C:5]2[CH2:6][CH:7]([C:10]3[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=3)[CH2:8][O:9][C:4]=2[C:3]=1[CH3:20]

Participants

7

Reactant 3

HCID 297MethaneHCID 521998p-Toluenesulfonic acid monohydrateHCID 21270160HCID 21270160, compound

Product 1

HCID 21270140HCID 21270140, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 312751,4-DioxaneSolvent

Procedure

7-Hydroxy-8-methyl-3-(4-methylphenyl)-4H-1-benzopyran-4-one (400 mg) in a mixture of dioxane and ethanol 1:1 (200 ml) is hydrogenated for 64 h at room temperature over palladium 10% on active charcoal (100 mg) in the presence of p-toluenesulfonic acid monohydrate (120 mg). After filtration of the catalyst, the filtrate is evaporated under reduced pressure to a volume of about 50 ml. Water (150 ml) is added and the solution is extracted with dichloromethane (3×100 ml). The combined organic solutions are washed with water, dried and evaporated. The product is dried in vacuo to constant weight to yield 3,4-dihydro-7-hydroxy-8-methyl-3-(4-methylphenyl)-2H-1-benzopyran, m.p. 136°-137°.

Workup

  1. filtrationAfter filtration of the catalyst
  2. customthe filtrate is evaporated under reduced pressure to a volume of about 50 ml
  3. additionWater (150 ml) is added
  4. extractionthe solution is extracted with dichloromethane (3×100 ml)
  5. washThe combined organic solutions are washed with water
  6. customdried
  7. customevaporated
  8. customThe product is dried in vacuo to constant weight

Sources & evidence

ORD record
ord-eff439e66199413a949589a4c5379f67
Source dataset
uspto-grants-1989_03
Patent number
US04814346

Reaction notes

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