Water → (2,3-Bis{[2-(methyloxy)ethyl]oxy}phenyl)methanol

HRID 253240ノート

反応式

HRID 253240 の反応式
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[C:15]([O:16][CH2:17][CH2:18][O:19][CH3:20])=[CH:14][CH:13]=[CH:12][C:7]=1[C:8](OC)=[O:9].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>C1COCC1>[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[C:15]([O:16][CH2:17][CH2:18][O:19][CH3:20])=[CH:14][CH:13]=[CH:12][C:7]=1[CH2:8][OH:9]

参加物

6

反応物 4

HCID 962Water2 回HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 66888836Methyl 2,3-bis{[2-(methyloxy)ethyl]oxy}benzoate

生成物 1

HCID 66889790(2,3-Bis{[2-(methyloxy)ethyl]oxy}phenyl)methanol収率 63%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a solution of methyl 2,3-bis{[2-(methyloxy)ethyl]oxy}benzoate (2.0 g, 7.03 mmol) in dry THF (10 mL) was added dropwise a 1M solution of lithium aluminum hydride in THF (7.0 mL), and the resulting mixture was stirred at rt for 1 h. Then, water (0.27 mL) was added slowly, followed by 15% aqueous sodium hydroxide (0.27 mL), and more water (0.81 mL). The mixture was filtered, the filter cake washed with ethyl acetate, and the combined filtrate was concentrated. Column chromatography on silica (1:1 hexanes/ethyl acetate) gave (2,3-bis{[2-(methyloxy)ethyl]oxy}phenyl)methanol (1.13 g, 63% yield) as a colorless oil. 1H NMR (400 MHz, CDCl3) δ6.96 (dd, 1H), 6.86 (m, 2H), 4.60 (d, 1H), 4.33 (m, 2H), 4.24 (t, 1H), 4.13 (m, 2H), 3.75 (m, 2H), 3.70 (m, 2H), 3.43 (s, 6H).

後処理

  1. filtrationThe mixture was filtered
  2. washthe filter cake washed with ethyl acetate
  3. concentrationthe combined filtrate was concentrated

出典と根拠

ORDレコード
ord-fc99ee0a0a8c439e8b95bab77c111a7d
出典データセット
uspto-grants-2011_01
特許番号
US07872014B2

反応ノート

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