2,3-Dihydroxybutanedioic Acid → HCID 23195084, compound

HRID 1941535Notes

Reaction equation

HRID 1941535 reaction equation
[CH2:1]([O:3][CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[N+:12]([O-])=O)[CH3:2].S(=O)(=O)(O)[OH:16].[Al].C(O)(=O)C(C(C(O)=O)O)O>O.C(OCC)(=O)C>[CH2:1]([O:3][CH2:4][CH2:5][C:6]1[CH:11]=[C:10]([OH:16])[CH:9]=[CH:8][C:7]=1[NH2:12])[CH3:2]

Participants

7

Reactant 4

HCID 8752,3-Dihydroxybutanedioic AcidHCID 1118Sulfuric AcidHCID 5359268AluminumHCID 19607201HCID 19607201, compound

Product 1

HCID 23195084HCID 23195084, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

58.5 g (0.3 mole) of 1-(β-ethoxyethyl)2-nitrobenzene was added at a temperature of 90° C. to a solution of 100 ml of concentrated sulphuric acid diluted in 1 liter of distilled water. 17 g of aluminium powder was added using a spatula and with vigourous stirring. Stirring was maintained for 40 minutes and then 70 g of tartaric acid was added. Stirring was continued for a further 15 minutes with the temperature maintained at 90° C. and then the reaction medium was cooled and the suspension filtered through sintered glass. The filtrate was neutralised with 20% ammonium hydroxide at a temperature below 20° C. A pinkish beige precipitate was obtained. The precipitate was taken up in 0.5 l of refluxing ethyl acetate, hot filtered and dry concentrated. It was recrystallised again from ethyl acetate to obtain beige crystals of the expected product which had a melting point of 102° C.

Workup

  1. temperaturewas maintained for 40 minutes
  2. stirringStirring
  3. temperaturethe reaction medium was cooled
  4. filtrationthe suspension filtered through sintered glass
  5. customwas neutralised with 20% ammonium hydroxide at a temperature below 20° C
  6. customA pinkish beige precipitate was obtained
  7. filtrationhot filtered
  8. customdry
  9. concentrationconcentrated
  10. customIt was recrystallised again from ethyl acetate

Sources & evidence

ORD record
ord-d6cd00a9eafb43f1ac02f1bc1f51ecd2
Source dataset
uspto-grants-1997_12
Patent number
US05703266

Reaction notes

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