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

HRID 78306

反応式

HRID 78306 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-bb3abe07a2b04f53bf762bd6d2d10bed
出典データセット
uspto-grants-2014_09
特許番号
US08841330B2

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