Nitric Acid → HCID 20189570, compound

HRID 1789063Notes

Reaction equation

HRID 1789063 reaction equation
[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[CH:7][CH:6]=[CH:5][C:4]=1[OH:11].[OH-].[K+].Cl[CH:15]([F:17])[F:16].[N+:18]([O-])([OH:20])=[O:19]>O1CCOCC1.O.CC1C(C)=CC2N([C@H]3O[C@@H](CO)C(OP(O[C@@H](CNC(CC[C@]4(C)[C@@H](CC(N)=O)[C@H]5[N-]C4=C(C)C4=NC(C(C)(C)[C@@H]4CCC(N)=O)=CC4=NC([C@](CC(N)=O)(C)[C@@H]4CCC(N)=O)=C(C)C4=N[C@]5(C)[C@](CC(N)=O)(C)[C@@H]4CCC(N)=O)=O)C)([O-])=O)C3O)C=NC=2C=1.O.[Co+2].C1CCCCC1.C(OCC)(=O)C>[F:16][CH:15]([F:17])[O:11][C:4]1[CH:5]=[C:6]([N+:18]([O-:20])=[O:19])[CH:7]=[C:8]([O:9][CH3:10])[C:3]=1[O:2][CH3:1]

Participants

8

Reactant 4

HCID 944Nitric AcidHCID 6372ChlorodifluoromethaneHCID 14797Potassium HydroxideHCID 788282,3-Dimethoxyphenol

Product 1

HCID 20189570HCID 20189570, compoundYield 48%

Reagents, catalysts & solvents 3

HCID 131715232HCID 131715232, compoundCatalystHCID 21867204Cyclohexane ethylacetateSolventHCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

50 g of 2,3-dimethoxyphenol are reacted analogously to Example B12a with 80 g of potassium hydroxide and chlorodifluoromethane in dioxane/water. The mixture is extracted with diisopropyl ether by shaking, the extract is washed with sodium hydroxide solution and 35 g of a product (b.p. 70°-74° C./0.3 mbar) are obtained which is reacted with 100% nitric acid analogously to Example B7b. The reaction product is subjected to chromatography on a silica gel column with cyclohexane/ethyl acetate (3:2), after which 1-difluoromethoxy-2,3-dimethoxy-5-nitrobenzene (m.p. 72°-73° C.) is isolated in 48% yield.

Workup

  1. extractionThe mixture is extracted with diisopropyl ether
  2. washthe extract is washed with sodium hydroxide solution and 35 g of a product (b.p. 70°-74° C./0.3 mbar)
  3. customare obtained which

Sources & evidence

ORD record
ord-0b49246c61754d2eb5f40629087f96d0
Source dataset
uspto-grants-1987_08
Patent number
US04686230

Reaction notes

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