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Sulfuric Acid → 2-Acetoxy-3-chloro-benzoic acid

HRID 2190906
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HRID 2190906 반응식
[OH:1][C:2]1[C:10]([Cl:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[C:12](OC(=O)C)(=[O:14])[CH3:13].OS(O)(=O)=O>>[C:12]([O:1][C:2]1[C:10]([Cl:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5])(=[O:14])[CH3:13]
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참가 물질

4

반응물 3

HCID 1118Sulfuric AcidHCID 7918Acetic AnhydrideHCID 745853-Chlorosalicylic acid

생성물 1

HCID 181834362-Acetoxy-3-chloro-benzoic acid수율 94.6%

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온도
100 °C

실험 절차

To a mixture of 2-hydroxy-3-chloro-benzoic acid (5.0 g, 29.0 mmol) in acetic anhydride (9.0 mL, 95.6 mmol) was added conc. H2SO4 (0.44 mL) at rt. Resulting suspension was heated in a 100° C. oil bath for 40 min. After cooled to about 50° C., the reaction mixture was poured onto ice (100 g) with stirring. Liquid was decanted off and the gooey residue was dissolved in methylene chloride, washed with water and brine, and dried over MgSO4. It was then filtered, and concentrated to give the title compound (5.89 g). 1H NMR (200 MHz, CDCl3): δ (ppm)=7.99 (dd, J=7.8, 1.6 Hz, 1H), 7.66 (dd, J=7.8, 1.6 Hz, 1H), 7.28 (m, 1H), 2.39 (s, 3H).

후처리

  1. customResulting suspension
  2. temperatureAfter cooled to about 50° C.
  3. additionthe reaction mixture was poured onto ice (100 g)
  4. customLiquid was decanted off
  5. dissolutionthe gooey residue was dissolved in methylene chloride
  6. washwashed with water and brine
  7. dry with materialdried over MgSO4
  8. filtrationIt was then filtered
  9. concentrationconcentrated

출처 및 근거

ORD 기록
ord-bbedcedd2850448cbea0c92fba9b1dde
출처 데이터셋
uspto-grants-2012_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08324405B2

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