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

HRID 598436Notes

Reaction equation

HRID 598436 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.

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-b0fe5798924c4979840d8cc6655614cd
Source dataset
uspto-grants-2011_03
Patent number
US07897623B2

Reaction notes

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