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Hydrochloric Acid → Methanesulfonic acid 4-hydroxymethyl-phenyl ester

HRID 1628131
ノート
印刷プレビュー

反応式

HRID 1628131 の反応式
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
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 10466383Benzoic acid, 4-[(methylsulfonyl)oxy]-, methyl esterHCID 21226445Aluminium lithium hydride2 回

生成物 1

HCID 85989572Methanesulfonic acid 4-hydroxymethyl-phenyl ester収率 93%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-799f86f65dc74ba5960c971967a6aea3
出典データセット
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08785681B2

反応ノート

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