Methanol → Methyl 3-acetylbenzoate

HRID 912036노트

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HRID 912036 반응식
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

참가 물질

6

반응물 4

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

생성물 1

HCID 15094405Methyl 3-acetylbenzoate

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
70 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-544aef6706cf4f8bb2241eae6dbba859
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08022206B2

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