Methyl dichloroacetate → HCID 66929700, compound

HRID 1983991Notes

Reaction equation

HRID 1983991 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([OH:11])[C:7](=[CH:9][CH:10]=1)[OH:8])([O-:3])=[O:2].[H-].[Na+].Cl[CH:15](Cl)[C:16]([O:18][CH3:19])=[O:17]>CN(C=O)C>[N+:1]([C:4]1[CH:10]=[CH:9][C:7]2[O:8][CH:15]([C:16]([O:18][CH3:19])=[O:17])[O:11][C:6]=2[CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 8315Methyl dichloroacetateHCID 24758Sodium hydrideHCID 35051094-Nitrocatechol

Product 1

HCID 66929700HCID 66929700, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

31.0 g of 4-nitrocatechol was added to 17.6 g of 60% NaH in suspension in 300 ml of DMF over 1 hour, with cooling to keep the temperature below 30° C. Stirring was continued for 15 minutes then 104 ml of methyl dichloroacetate was added over 1 hour, and stirring was continued for 4 hours at 90° C. The reaction medium was poured over a mixture of 2 liters of ice/water then extracted 4 times with 400 ml of AcOEt. The combined organic phases were washed once with a saturated NaCl solution then dried and concentrated under vacuum (DMF evaporated off). The residue was taken up in a AcOEt/H2O mixture and the pH was brought to 8.6 using Na2CO3; the organic phase was decanted, washed with saturated NaHCO3, H2O, 5% KHSO4/K2SO4, H2O, saturated NaCl then dried and vacuum evaporated; a semi-solid residue was obtained which was taken up then triturated in heptane to produce a solid. m=27.7 g, MP=90-92° C.

Workup

  1. temperaturewith cooling
  2. customthe temperature below 30° C
  3. stirringstirring
  4. waitwas continued for 4 hours at 90° C
  5. extractionthen extracted 4 times with 400 ml of AcOEt
  6. washThe combined organic phases were washed once with a saturated NaCl solution
  7. customthen dried
  8. concentrationconcentrated under vacuum (DMF evaporated off)
  9. customthe organic phase was decanted
  10. washwashed with saturated NaHCO3, H2O, 5% KHSO4/K2SO4, H2O, saturated NaCl
  11. customthen dried
  12. customvacuum evaporated
  13. customa semi-solid residue was obtained which
  14. customwas taken up then triturated in heptane
  15. customto produce a solid

Sources & evidence

ORD record
ord-99496da87a5f4089996976aaf2286b38
Source dataset
uspto-grants-2009_06
Patent number
US07544682B2

Reaction notes

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