Hydrochloric Acid → [3-(3-Formyl-4-nitro-phenoxy)-phenyl]-carbamic acid benzyl ester

HRID 1968808Notes

Reaction equation

HRID 1968808 reaction equation
Cl.[CH2:2]([O:9][C:10](=[O:33])[NH:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([O:18][C:19]2[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[C:21]([CH:28](OC)[O:29]C)[CH:20]=2)[CH:13]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>C1COCC1.O>[CH2:2]([O:9][C:10](=[O:33])[NH:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([O:18][C:19]2[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[C:21]([CH:28]=[O:29])[CH:20]=2)[CH:13]=1)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 58625141[3-(3-Dimethoxymethyl-4-nitro-phenoxy)-phenyl]-carbamic acid benzyl ester

Product 1

HCID 58625118[3-(3-Formyl-4-nitro-phenoxy)-phenyl]-carbamic acid benzyl ester

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

12N HCl (33 mL) and water (66 mL) were added to a mixture of [3-(3-dimethoxymethyl-4-nitro-phenoxy)-phenyl]-carbamic acid benzyl ester (0.14 mol) in THF (400 mL) and the reaction mixture was stirred for 48 hours at room temperature. The mixture was diluted with H2O (500 mL) and extracted 2 times with diisopropyl ether. The organic layer was separated, dried (MgSO4), filtered off and the solvent was evaporated. The resulting product was removed with a spatula and dried under vacuum to yield the title compound as a residue.

Workup

  1. extractionextracted 2 times with diisopropyl ether
  2. customThe organic layer was separated
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered off
  5. customthe solvent was evaporated
  6. customThe resulting product was removed with a spatula
  7. customdried under vacuum

Sources & evidence

ORD record
ord-5d4ede84ef604afe9e71491ce7be0bc5
Source dataset
uspto-grants-2013_04
Patent number
US08426429B2

Reaction notes

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