Hydrochloric Acid → 2-(3-Methylthiophen-2-YL)acetic acid

HRID 1866094ノート

反応式

HRID 1866094 の反応式
O.NN.C[O:5][C:6](=[O:15])[C:7]([C:9]1[S:10][CH:11]=[CH:12][C:13]=1[CH3:14])=O.[OH-].[K+].Cl>C(O)COCCO.O>[CH3:14][C:13]1[CH:12]=[CH:11][S:10][C:9]=1[CH2:7][C:6]([OH:15])=[O:5]

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 21843477Methyl 2-(3-methylthiophen-2-yl)-2-oxoacetate

生成物 1

HCID 127650662-(3-Methylthiophen-2-YL)acetic acid収率 66%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8117Diethylene Glycol溶媒

反応条件

温度
3040 °C

実験手順

112.5 ml (116 g, 2.312 mol) of hydrazine hydrate were added slowly to a solution of 90 g (0.489 mol) of methyl(3-methylthiophen-2-yl)oxoacetate in 260 ml of diethylene glycol, and the mixture was heated under reflux for 30 min. After cooling to 3040° C., 82 g (1.246 mol) of potassium hydroxide were added a little at a time, which was accompanied by a temperature increase to 70-80° C. with simultaneous evolution of nitrogen. The mixture was then slowly heated to reflux and stirred at this temperature for a total of 5 h. After cooling to room temperature, the mixture was poured into 2 l of water, adjusted to pH=1 using 250 ml of semi-concentrated hydrochloric acid and extracted with ethyl acetate. The organic phase was dried over magnesium sulphate and filtered off and the solvent was removed, which gave 50 g of (3-methylthiophen-2-yl)acetic acid. Yield: 66%. 1H-NMR (DMSO): δ=7.25 (d, 1H), 6.84 (d, 2H), 3.67 (s, 2H), 2.11 (s, 3H).

後処理

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 30 min
  3. temperatureincrease to 70-80° C. with simultaneous evolution of nitrogen
  4. temperatureThe mixture was then slowly heated
  5. temperatureto reflux
  6. temperatureAfter cooling to room temperature
  7. extractionextracted with ethyl acetate
  8. dry with materialThe organic phase was dried over magnesium sulphate
  9. filtrationfiltered off
  10. customthe solvent was removed

出典と根拠

ORDレコード
ord-17e47cb4cd8e4328a90372266f4156fb
出典データセット
uspto-grants-2009_12
特許番号
US07629294B2

反応ノート

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