Dimethyl Sulfate → Methyl 2-methoxy-3-methylbenzoate

HRID 2186636

反応式

HRID 2186636 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 SulfateHCID 67383-Methylsalicylic AcidHCID 11430Potassium Carbonate

生成物 1

HCID 13229229Methyl 2-methoxy-3-methylbenzoate収率 91%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

To a mixture of 3-methyl-salicylic acid (1.32 mol)and anhydrous potassium carbonate (3.6 mol)dissolved in 3.5 L of dry acetone in a 5L round bottle flask, dimethylsulfate (2.2 mol) was added in several times. The mixture was refluxed overnight, and the reaction was monitored by TLC. After filtration of the reaction mixture, the solvents of the filtrate were evaporated and 215 g of a pale yellow thick oil was obtained as the raw product. Yield 91%. 1H NMR (500 MHz, CDCl3, 25° C.) δ: 2.263 (s, 3H, CH3), 3.782 (s, 3H, OCH3), 3.854 (s, 3H, OCH3), 6.984 (t, J=7.5, 1H, ArH), 7.276 (d, J=7.5, 1H, ArH), 7.582 (d, J=7.5, 1H, ArH); 13C NMR (500 MHz, CDCl3, 25° C.) δ: 15.72, 51.81, 61.17, 123.26, 124.36, 128.86, 132.46, 134.88, 158.16, 166.61.

後処理

  1. additionwas added in several times
  2. temperatureThe mixture was refluxed overnight
  3. filtrationAfter filtration of the reaction mixture
  4. customthe solvents of the filtrate were evaporated

出典と根拠

ORDレコード
ord-fcf342dbae20466ea760de9c24770926
出典データセット
uspto-grants-2002_06
特許番号
US06406297B1

関連ノート

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