Hydrochloric Acid → HCID 18694851, compound

HRID 1871062Notes

Reaction equation

HRID 1871062 reaction equation
C[O-].[Na+].[N+](C(C)C)([O-])=[O:5].Br[CH2:11][C:12]1[C:13]([Cl:24])=[C:14]([CH:19]=[CH:20][C:21]=1[O:22][CH3:23])[C:15]([O:17][CH3:18])=[O:16].Cl>CO>[Cl:24][C:13]1[C:12]([CH:11]=[O:5])=[C:21]([O:22][CH3:23])[CH:20]=[CH:19][C:14]=1[C:15]([O:17][CH3:18])=[O:16]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3982-NitropropaneHCID 10942334Sodium MethoxideHCID 18694859HCID 18694859, compound

Product 1

HCID 18694851HCID 18694851, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To 40 ml methanol, was added 28% methanol solution of sodium methylate in an amount of 5.4 g and the resulting mixture was then fed dropwise with 2-nitropropane in an amount of 2.5 g at an ambient temperature. Then, the mixture was further added with methyl 3-bromomethyl-2-chloro-4-methoxybenzoate in an amount of 7.5 g and stirred for an hour under reflux and heating. After cooling the mixture, the reacted-mixture was added with 100 ml 1N-hydrochloric acid and then extracted with ethyl acetate. The ethyl acetate layer obtained was washed with saturated saline solution and dried with anhydrous magnesium sulfate. The solvent remained in the layer was condensed under reduced pressure to obtain crystals. The crystals obtained were then washed with ethyl ether to obtain methyl 2-chloro-3-formyl-4-methoxybenzoate in an amount of 3.1 g in crystalline form. The yield was 54%.

Workup

  1. temperatureunder reflux
  2. temperatureheating
  3. temperatureAfter cooling the mixture
  4. extractionextracted with ethyl acetate
  5. customThe ethyl acetate layer obtained
  6. washwas washed with saturated saline solution
  7. dry with materialdried with anhydrous magnesium sulfate
  8. customcondensed under reduced pressure
  9. customto obtain crystals
  10. customThe crystals obtained
  11. washwere then washed with ethyl ether

Sources & evidence

ORD record
ord-3022fa8a2d894e9585d5f0255b71b3ab
Source dataset
uspto-grants-2000_08
Patent number
US06100421

Reaction notes

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