2,5-Dihydroxybenzoic acid → 4-(3-Methoxycarbonyl-4-methoxyphenoxy)-1-nitrobenzene

HRID 1768280Notes

Reaction equation

HRID 1768280 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([CH:17]=[CH:18][C:19]=1O)[O:7][C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=1)([OH:3])=[O:2].O[C:22]1C=CC(O)=CC=1C(O)=O.C([O-])([O-])=O.[K+].[K+].S([O:43][CH3:44])(OC)(=O)=O>CC(C)=O>[CH3:22][O:3][C:1]([C:4]1[CH:5]=[C:6]([CH:17]=[CH:18][C:19]=1[O:43][CH3:44])[O:7][C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=1)=[O:2]

Participants

6

Reactant 4

HCID 34692,5-Dihydroxybenzoic acidHCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 214925045-(4-Nitrophenoxy)-salicylic acid

Product 1

HCID 230230954-(3-Methoxycarbonyl-4-methoxyphenoxy)-1-nitrobenzene

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 4-(3-carboxy-4-hydroxyphenoxy)-1-nitrobenzene (prepared from 2,5-dihydroxybenzoic acid in a manner analogous to that described in Method A13, Step 1, 12 mmol) in acetone (50 mL) was added K2CO3 (5 g) and dimethyl sulfate (3.5 mL). The resulting mixture was heated at the reflux temp. overnight, then cooled to room temp. and filtered through a pad of Celite®. The resulting solution was concentrated under reduced pressure, absorbed onto SiO2, and purified by column chromatography (50% EtOAc/50% hexane) to give 4-(3-methoxycarbonyl-4-methoxyphenoxy)-1-nitrobenzene as a yellow powder (3 g): mp 115-118° C. Step 2. 4-(3-Carboxy-4-methoxyphenoxy)-1-nitrobenzene:

Workup

  1. temperatureThe resulting mixture was heated at the reflux temp
  2. temperatureovernight, then cooled to room temp.
  3. filtrationfiltered through a pad of Celite®
  4. concentrationThe resulting solution was concentrated under reduced pressure
  5. customabsorbed onto SiO2
  6. custompurified by column chromatography (50% EtOAc/50% hexane)

Sources & evidence

ORD record
ord-f030adba8ce04682866e21d33cf7f38a
Source dataset
uspto-grants-2007_06
Patent number
US07235576B1

Reaction notes

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