Sodium Carbonate → 4,5-Dimethoxyphthalic acid

HRID 571272

反応式

HRID 571272 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[C:8](=[O:14])[O:7]C2.[O-][Mn](=O)(=O)=O.[K+].[C:21]([O-:24])([O-:23])=O.[Na+].[Na+]>O>[CH3:13][O:12][C:11]1[CH:10]=[C:9]([C:8]([OH:14])=[O:7])[C:5](=[CH:4][C:3]=1[O:2][CH3:1])[C:21]([OH:24])=[O:23]

参加物

5

反応物 3

HCID 10340Sodium CarbonateHCID 2304605,6-Dimethoxy-3H-isobenzofuran-1-oneHCID 516875Potassium Permanganate

生成物 1

HCID 2909884,5-Dimethoxyphthalic acid収率 18.2%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

5,6-Dimethoxyisobenzofuran-1(3H)-one (3.171 g, 16.33 mmol) was treated with a solution of KMnO4 (2.57 g, 16.26 mmol) and Na2CO3 (1.542 g, 14.55 mmol) in water (110 ml). The solution was stirred at room temperature for 24 hours, then insoluble material was removed by filtration. The filtrate was cooled with an ice-water bath and acidified with concentrated aqueous HCl. The acidic solution was extracted three times with ethyl acetate (500 ml). The combined organic layers were dried over sodium sulfate and evaporated to dryness to give 600 mg of desired compound. The aqueous phase was then concentrated to 20 ml and a white solid precipitated. After filtration 500 mg desired compound were recovered. The two portions were collected to afford 4,5-dimethoxyphthalic acid as a white powder (1.1 g, 4.87 mmol, 30% yield). MS/ESI+ not detectable [MH]+.

後処理

  1. custominsoluble material was removed by filtration
  2. temperatureThe filtrate was cooled with an ice-water bath
  3. extractionThe acidic solution was extracted three times with ethyl acetate (500 ml)
  4. dry with materialThe combined organic layers were dried over sodium sulfate
  5. customevaporated to dryness

出典と根拠

ORDレコード
ord-33b7fb174bd34192a55661656096ddcd
出典データセット
uspto-grants-2015_05
特許番号
US09024027B2

関連ノート

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