Dimethyl Sulfate → Methyl 2-methoxy-3-methylbenzoate

HRID 1921915

反応式

HRID 1921915 の反応式
[CH3:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:4]([C:5]([OH:7])=O)[C:3]=1[OH:11].[C:12](=O)([O-])[O-].[K+].[K+].COS([O:23][CH3:24])(=O)=O>CC(C)=O>[CH3:12][O:11][C:3]1[C:2]([CH3:1])=[CH:10][CH:9]=[CH:8][C:4]=1[C:5]([O:23][CH3:24])=[O:7]

参加物

5

反応物 3

HCID 6497Dimethyl Sulfate2 回HCID 67383-Methylsalicylic AcidHCID 11430Potassium Carbonate2 回

生成物 1

HCID 13229229Methyl 2-methoxy-3-methylbenzoate

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

To a mixture of 3-methyl-salicylic acid (200 g, 1.32 mol), anhydrous potassium carbonate (500 gram, 3.6 mol) and dry acetone (3.5 L) in a 5 liter round bottle flask, dimethylsulfate (DMS, 210 mL, 2.2 mol) was added in several portions. After stirring at room temperature overnight, the mixture was heated at reflux, and the reaction was monitored by TLC. In order to complete the etherification, further additions of DMS and K2CO3 may be necessary. When TLC indicated the completion of the reaction, the mixture was refluxed 4 more hours to destroy any remaining DMS. The mixture was filtered, and the filtrate was evaporated to remove the solvents. A pale yellow thick oil was obtained as the raw product, yield 215 g (91%). 1H NMR (500 MHz, CDCl3, 25° C.) δ: 2.26 (s, 3H, CH3), 3.78 (s, 3H, OCH3), 3.85 (s, 3H, OCH3), 6.98 (t, J=7.5, 1H, ArH), 7.27 (d, J=7.5, 1H, ArH), 7.58 (d, J=7.5, 1H, ArH); 13C NMR (500 MHz, CDCl3, 25° C.) δ: 15.7, 51.8, 61.1, 123.2, 124.3, 128.8, 132.4, 134.8, 158.1, 166.6.

後処理

  1. temperaturethe mixture was heated
  2. temperatureat reflux
  3. customthe completion of the reaction
  4. temperaturethe mixture was refluxed 4 more hours
  5. customto destroy any remaining DMS
  6. filtrationThe mixture was filtered
  7. customthe filtrate was evaporated
  8. customto remove the solvents

出典と根拠

ORDレコード
ord-28af11f704094426a869ba0dc6830139
出典データセット
uspto-grants-2012_05
特許番号
US08173800B2

関連ノート

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