Cerate(2-), hexakis(nitrato-kappaO)-, potassium (1:2), (OC-6-11)- → Methyl rac-1,2,3,4,5,8-hexahydro-5,8-dioxonaphthalene-2-carboxylate

HRID 462616Notes

Reaction equation

HRID 462616 reaction equation
[N+]([O-])(O)=O.[N+]([O-])(O)=O.[N+]([O-])(O)=O.[N+]([O-])(O)=O.[N+]([O-])(O)=O.[N+]([O-])(O)=O.[Ce].C[O:27][C:28]1[CH:37]=[CH:36][C:35]([O:38]C)=[C:34]2[C:29]=1[CH2:30][CH2:31][CH:32]([C:40]([O:42][CH3:43])=[O:41])[CH2:33]2>O.C(#N)C>[O:27]=[C:28]1[CH:37]=[CH:36][C:35](=[O:38])[C:34]2[CH2:33][CH:32]([C:40]([O:42][CH3:43])=[O:41])[CH2:31][CH2:30][C:29]1=2

Participants

5

Reactant 2

HCID 407333Cerate(2-), hexakis(nitrato-kappaO)-, potassium (1:2), (OC-6-11)-HCID 14409652Methyl 5,8-dimethoxy-1,2,3,4-tetrahydronaphthalene-2-carboxylate

Product 1

HCID 20283297Methyl rac-1,2,3,4,5,8-hexahydro-5,8-dioxonaphthalene-2-carboxylateYield 98.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent

Procedure

A solution of 19.74 g (0.036 mol) of ammonium ceric nitrate in 120 ml of water was added to a stirred solution of 3.00 g (0.012 mol) of methyl rac-1,2,3,4-tetrahydro-5,8-dimethoxynaphthalene-2-carboxylate in 54 ml of acetonitrile. The mixture was stirred at room temperature for 25 minutes and then diluted with 150 ml of water. The solution was extracted with three 150 ml portions of diethyl ether and the combined diethyl ether extracts were washed with 150 ml of water, dried and evaporated to yield 2.60 g (98.5%) of methyl rac-1,2,3,4,5,8-hexahydro-5,8-dioxonaphthalene-2-carboxylate in the form of a bright yellow solid of melting point 41°-42° C.

Workup

  1. extractionThe solution was extracted with three 150 ml portions of diethyl ether
  2. washthe combined diethyl ether extracts were washed with 150 ml of water
  3. customdried
  4. customevaporated

Sources & evidence

ORD record
ord-f8978937e703443f866f94b2e83f62b4
Source dataset
uspto-grants-1985_05
Patent number
US04515969

Reaction notes

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