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Pyridine → Benzoic acid, 4-[(methylsulfonyl)oxy]-, methyl ester

HRID 709444
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HRID 709444 반응식
[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.N1C=CC=CC=1.[CH3:18][S:19](Cl)(=[O:21])=[O:20]>C1COCC1>[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][C:7]([O:10][S:19]([CH3:18])(=[O:21])=[O:20])=[CH:6][CH:5]=1
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참가 물질

5

반응물 3

HCID 1049PyridineHCID 7456MethylparabenHCID 31297Methanesulfonyl chloride

생성물 1

HCID 10466383Benzoic acid, 4-[(methylsulfonyl)oxy]-, methyl ester수율 95.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

4-Hydroxybenzoic acid methylester (2.29 g, 20 mmol) was dissolved together with pyridine (2.02 mL, 25 mmol) in anhydrous THF (20 mL) and after cooling down to 0° C., methanesulfonyl chloride (2.16 mL, 21 mmol) was added dropwise. After complete addition the ice bath was removed and the mixture was stirred at room temperature for 5 h. The slurry was diluted with DCM and extracted with H2O and aq. HCl (2N). The separated organic layer was finally dried (MgSO4) and evaporated to afford the crude product as an oil (4.38 g, 95%). 1H NMR (400 MHz, CDCl3): δ 8.07-8.09 (d, 2H), 7.32-7.34 (d, 2H), 3.90 (s, 3H), 3.16 (s, 3H).

후처리

  1. customwas removed
  2. additionThe slurry was diluted with DCM
  3. extractionextracted with H2O and aq. HCl (2N)
  4. dry with materialThe separated organic layer was finally dried (MgSO4)
  5. customevaporated

출처 및 근거

ORD 기록
ord-fc636999ff8a4c9eb5f547d56b36c282
출처 데이터셋
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09181181B2

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