Hydrochloric Acid → HCID 21948885, compound

HRID 2215477Notes

Reaction equation

HRID 2215477 reaction equation
[OH:1][C:2]1[C:9]([OH:10])=[C:8]([N+:11]([O-:13])=[O:12])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].Br[CH2:15]Cl.C(=O)([O-])[O-].[Cs+].[Cs+].Cl>CN(C=O)C>[N+:11]([C:8]1[C:9]2[O:10][CH2:15][O:1][C:2]=2[C:3]([CH:4]=[O:5])=[CH:6][CH:7]=1)([O-:13])=[O:12]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6333BromochloromethaneHCID 10796Cesium carbonateHCID 10442360Benzaldehyde, 2,3-dihydroxy-4-nitro-

Product 1

HCID 21948885HCID 21948885, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

14.2 g of 2,3-dihydroxy-4-nitrobenzaldehyde in 1000 ml of DMF is stirred with 57.6 ml of bromochloromethane and 50.6 g of cesium carbonate at 100° C. for 7 hours. The batch is added to 1 N hydrochloric acid and extracted with ethyl acetate. The organic phase is washed several times with water and brine, dried with sodium sulfate and concentrated by evaporation in a vacuum. The brown solid that is obtained is purified by column chromatography (silica gel, hexane/ethyl acetate 100:0->60:40). 7.4 g of 7-nitro-benzo[1,3]dioxole-4-carbaldehyde is obtained as a light yellow solid. The latter is mixed in 400 ml of acetone at 10° C. with a solution of 11.8 g of potassium permanganate in 190 ml of acetone/water (1:1). It was stirred for 10 hours, added to 2 N hydrochloric acid and filtered through diatomaceous earth. The acetone is removed in a vacuum, and the aqueous phase is made alkaline with sodium hydroxide solution. It is extracted with ether, and then the aqueous phase is acidified with hydrochloric acid. It is extracted with ethyl acetate, washed with water, dried with sodium sulfate and concentrated by evaporation in a vacuum. 4.36 g of 7-nitro-benzo[1,3]dioxole-4-carboxylic acid is obtained as a brown solid, flash point 230–239° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic phase is washed several times with water and brine
  3. dry with materialdried with sodium sulfate
  4. concentrationconcentrated by evaporation in a vacuum
  5. customThe brown solid that is obtained
  6. customis purified by column chromatography (silica gel, hexane/ethyl acetate 100:0->60:40)

Sources & evidence

ORD record
ord-e50ea9d2fcd34ee99142f57a3c930e17
Source dataset
uspto-grants-2006_09
Patent number
US07109212B2

Reaction notes

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