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Hydrochloric Acid → Methanesulfonic acid 4-hydroxymethyl-phenyl ester

HRID 1628131
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HRID 1628131 반응식
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][C:7]([O:10][S:11]([CH3:14])(=[O:13])=[O:12])=[CH:6][CH:5]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].Cl>C1COCC1>[OH:2][CH2:3][C:4]1[CH:5]=[CH:6][C:7]([O:10][S:11]([CH3:14])(=[O:13])=[O:12])=[CH:8][CH:9]=1
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참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 10466383Benzoic acid, 4-[(methylsulfonyl)oxy]-, methyl esterHCID 21226445Aluminium lithium hydride2회

생성물 1

HCID 85989572Methanesulfonic acid 4-hydroxymethyl-phenyl ester수율 93%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

4-Methanesulfonyloxy-benzoic acid methyl ester (330 mg, 1.43 mmol) was dissolved in anhyrous THF (10 mL) and LiAlH4 (109 mg, 2.86 mmol) was added. The resulting suspension was stirred at room temperature until no starting material was left. Excess LiAlH4 was hydrolyzed with aq. HCl (2N) and the remaining suspension was extracted with EtOAc. The organic layer was seperated, dried (MgSO4) and evaporated and the remaining crude product was purified by flash chromatography using n-heptane/EtOAc 3:7 as the eluent to afford the title compound as an oil (202 mg, 93%). 1H NMR (400 MHz, CDCl3): δ 7.37-7.40 (d, 2H), 7.23-7.25 (d, 2H), 4.67 (s br, 2H), 3.10 (s, 3H).

후처리

  1. waitwas left
  2. extractionthe remaining suspension was extracted with EtOAc
  3. customThe organic layer was seperated
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customthe remaining crude product was purified by flash chromatography

출처 및 근거

ORD 기록
ord-799f86f65dc74ba5960c971967a6aea3
출처 데이터셋
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08785681B2

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