Hydrochloric Acid → HCID 10827459, compound

HRID 259927Notes

Reaction equation

HRID 259927 reaction equation
[N+:1]([O-:4])([O-])=[O:2].[Na+].Cl.[Br:7][C:8]1[CH:16]=[C:15]([O:17][CH3:18])[C:11]([C:12]([OH:14])=[O:13])=[CH:10][C:9]=1[OH:19]>O.C(OCC)C>[Br:7][C:8]1[CH:16]=[C:15]([O:17][CH3:18])[C:11]([C:12]([OH:14])=[O:13])=[C:10]([N+:1]([O-:4])=[O:2])[C:9]=1[OH:19]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 24268Sodium NitrateHCID 10658112HCID 10658112, compound

Product 1

HCID 10827459HCID 10827459, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

Sodium nitrate (361 mg, 4.25 mmol) was dissolved in water (4 mL) and LaNO3 *6H2O (18 mg, 0.04 mmol) and HCl (12M, 4 mL) were added. The solution was cooled to 0° C. and a slurry of 4-bromo-3-hydroxy-6-methoxybenzoic acid in diethyl ether (20 mL) was added to the reaction mixture in portions during 10 min. After slowly raising the temperature to room temperature the mixture was stirred for 7 h. Extraction between H2O (20 mL) and CH2Cl2 (3×30 mL), drying the organic phase with MgSO4, filtration and evaporation under reduced pressure gave a mixture of products. Purification by silica gel chromatography (HOAc-EtOAc-toluene 1:2:8) gave the title compound (0.6 g). 1H NMR (CD3OD): δ7.57 (s, 1H), 3.85 (s, 3H). MS (EI, 70 eV): m/z (rel. int.) 291/293 (M+, 21/19).

Workup

  1. temperatureAfter slowly raising the temperature to room temperature the mixture
  2. extractionExtraction between H2O (20 mL) and CH2Cl2 (3×30 mL)
  3. customdrying the organic phase
  4. filtrationwith MgSO4, filtration and evaporation under reduced pressure
  5. customgave
  6. additiona mixture of products
  7. customPurification by silica gel chromatography (HOAc-EtOAc-toluene 1:2:8)

Sources & evidence

ORD record
ord-de1054a06697415a9966f71db990a2df
Source dataset
uspto-grants-1996_06
Patent number
US05523475

Reaction notes

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