Methanol → Methyl 3-acetylbenzoate

HRID 912036ノート

反応式

HRID 912036 の反応式
S(=O)(=O)(O)O.CO.[C:8]([C:11]1[CH:12]=[C:13]([CH:17]=[CH:18][CH:19]=1)[C:14]([OH:16])=[O:15])(=[O:10])[CH3:9].[C:20]([O-])(O)=O.[Na+]>O>[CH3:20][O:15][C:14](=[O:16])[C:13]1[CH:17]=[CH:18][CH:19]=[C:11]([C:8](=[O:10])[CH3:9])[CH:12]=1

参加物

6

反応物 4

HCID 887MethanolHCID 1118Sulfuric AcidHCID 2203243-Acetylbenzoic acidHCID 516892Sodium Bicarbonate

生成物 1

HCID 15094405Methyl 3-acetylbenzoate

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
70 °C

実験手順

Sulfuric acid (23.4 μl, 0.430 mmol) was added into the MeOH (15 ml) solution of 3-acetylbenzoic acid (720 mg, 4.30 mmol). The mixture was stirred at 70° C. for 20 h. After that time, the mixture was cooled and was treated with saturated NaHCO3 till pH>9, followed by adding water to dissolve the solid which was formed, extracted with EtOAc (2×50 ml). The extracts were washed with water (50 ml), brine (50 ml), dried over MgSO4, filtered and concentrated in vacuo, giving the title compound as brown oil. 1H NMR (400 MHz, CDCl3): δ=2.66 (s, 3H), 3.96 (s, 3H), 7.54-7.59 (m, 1H), 8.14-8.19 (m, 1H), 8.22-8.26 (m, 1H), 8.59-8.61 (m, 1H). MS (ES+): m/z 179.17 [MH+]. HPLC: tR=2.82 min (polar—5 min, ZQ3).

後処理

  1. temperatureAfter that time, the mixture was cooled
  2. dissolutionto dissolve the solid which
  3. customwas formed
  4. extractionextracted with EtOAc (2×50 ml)
  5. washThe extracts were washed with water (50 ml), brine (50 ml)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-544aef6706cf4f8bb2241eae6dbba859
出典データセット
uspto-grants-2011_09
特許番号
US08022206B2

反応ノート

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