Sodium Hydroxide → 3-(Methylthio)benzoic Acid

HRID 732021

反応式

HRID 732021 の反応式
C[O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([S:10][CH3:11])[CH:5]=1.[OH-].[Na+]>CO.C1COCC1>[CH3:11][S:10][C:6]1[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=1)[C:3]([OH:12])=[O:2]

参加物

5

反応物 2

HCID 14798Sodium HydroxideHCID 6432769Methyl 3-(methylthio)benzoate

生成物 1

HCID 2203293-(Methylthio)benzoic Acid収率 97%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

3-Methylsulfanyl-benzoic acid methyl ester (684 mg, 3.8 mmol) and 1N NaOH (5.6 mL, 5.6 mmol) in methanol (8 mL) and THF (8 mL) were heated at 70° C. for 1 hour. The reaction mixture was concentrated and then the residue was diluted with water. After acidification with 1N HCl to pH˜2, the aqueous layer was extracted with ethyl acetate and then washed with water and saturated brine, dried over anhydrous sodium sulfate, filtered, and concentrated to afford 3-methylsulfanyl-benzoic acid (616 mg, 97%, white solid). 1H NMR (DMSO), δ (ppm): 13.1 (bs, 1H), 7.76 (s, 1H), 7.70 (d, 1H), 7.51 (d, 1H), 7.44 (t, 1H), 2.52 (s, 3H).

後処理

  1. concentrationThe reaction mixture was concentrated
  2. additionthe residue was diluted with water
  3. extractionAfter acidification with 1N HCl to pH˜2, the aqueous layer was extracted with ethyl acetate
  4. washwashed with water and saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-1221c9dbbc8e4546a1539b6b538ac032
出典データセット
uspto-grants-2009_09
特許番号
US07585881B2

関連ノート

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