Nitric Acid → 5-[2-(3-Chloro-phenyl)-ethoxy]-4-methoxy-2-nitro-benzoic acid methyl ester

HRID 521455Notes

Reaction equation

HRID 521455 reaction equation
OC1C=C(C=CC=1OC)C(OC)=O.ClC1C=C(CCO)C=CC=1.[CH3:24][O:25][C:26](=[O:45])[C:27]1[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[C:29]([O:35][CH2:36][CH2:37][C:38]2[CH:43]=[CH:42][CH:41]=[C:40]([Cl:44])[CH:39]=2)[CH:28]=1.[N+:46]([O-])([OH:48])=[O:47]>>[CH3:24][O:25][C:26](=[O:45])[C:27]1[CH:28]=[C:29]([O:35][CH2:36][CH2:37][C:38]2[CH:43]=[CH:42][CH:41]=[C:40]([Cl:44])[CH:39]=2)[C:30]([O:33][CH3:34])=[CH:31][C:32]=1[N+:46]([O-:48])=[O:47]

Participants

5

Reactant 4

HCID 944Nitric AcidHCID 78856m-Chlorophenethylic alcoholHCID 4056967Methyl 3-hydroxy-4-methoxybenzoateHCID 670762963-[2-(3-Chloro-phenyl)-ethoxy]-4-methoxy-benzoic acid methyl ester

Product 1

HCID 670767915-[2-(3-Chloro-phenyl)-ethoxy]-4-methoxy-2-nitro-benzoic acid methyl ester

Procedure

Methyl 3-hydroxy-4-methoxybenzoate and 2-(3-chlorophenyl)-ethanol were reacted in analogy to step 1 of example 1. The obtained 3-[2-(3-chloro-phenyl)-ethoxy]-4-methoxy-benzoic acid methyl ester (0.750 g, 2.34 mmol) was added slowly to ice-cooled 100% nitric acid (10 ml). The ice bath was removed and stirring was continued overnight. The mixture was cautiously transferred into a stirred mixture of EA, water and an excess of sodium hydrogencarbonate and extracted with EA. The combined organic extracts were washed with a saturated sodium chloride solution, dried over sodium sulfate, filtered and evaporated to dryness. The solid residue was extracted with diethyl ether, and the ethereal solution was evaporated. The residue was stirred with HEP, and the solid was filtered and dried in vacuo to give 0.680 g of the title compound.

Workup

  1. customThe ice bath was removed
  2. additionThe mixture was cautiously transferred into a stirred mixture of EA, water
  3. extractionan excess of sodium hydrogencarbonate and extracted with EA
  4. washThe combined organic extracts were washed with a saturated sodium chloride solution
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated to dryness
  8. extractionThe solid residue was extracted with diethyl ether
  9. customthe ethereal solution was evaporated
  10. stirringThe residue was stirred with HEP
  11. filtrationthe solid was filtered
  12. customdried in vacuo

Sources & evidence

ORD record
ord-fc3fa8a1cef34d83aa89e4341f66f39d
Source dataset
uspto-grants-2016_05
Patent number
US09328071B2

Reaction notes

Loading…