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

HRID 253240노트

반응식

HRID 253240 반응식
[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]

참가 물질

6

반응물 4

HCID 962Water2회HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 66888836Methyl 2,3-bis{[2-(methyloxy)ethyl]oxy}benzoate

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-fc99ee0a0a8c439e8b95bab77c111a7d
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07872014B2

반응 노트

불러오는 중…