Hydrochloric Acid → HCID 85843028, compound

HRID 1770634Notes

Reaction equation

HRID 1770634 reaction equation
C[O:2][CH:3](OC)[C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[C:6]([N+:14]([O-:16])=[O:15])[CH:5]=1.Cl>CC(C)=O>[CH:3]([C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[C:6]([N+:14]([O-:16])=[O:15])[CH:5]=1)=[O:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86727012HCID 86727012, compound

Product 1

HCID 85843028HCID 85843028, compoundYield 91.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of methyl 4-dimethoxymethyl-2-nitrobenzoate (2 g, 7.8 mmol) in acetone (25 ml) was treated dropwise with hydrochloric acid (6M, 20 ml) and stirred for 2 hours. The solvent was removed under vacuo, the residue was then treated with water (25 ml) and extracted with ethyl acetate (2×50 ml). The combined organic layers were dried over sodium sulfate and concentrated to give methyl 4-formyl-2-nitrobenzoate (1.5 g). 1H-NMR (400 MHz, CDCl3): 10.10 (1H, s), 8.39-8.41 (1H, m), 8.16 (1H, d), 7.88 (1H, d), 3.94 (3H, s) ppm.

Workup

  1. customThe solvent was removed under vacuo
  2. additionthe residue was then treated with water (25 ml)
  3. extractionextracted with ethyl acetate (2×50 ml)
  4. dry with materialThe combined organic layers were dried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-bbb3c7e4049e4057b27390fc5b30af00
Source dataset
uspto-grants-2016_02
Patent number
US09247740B2

Reaction notes

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