Methyl 3,5-bis(methoxymethoxy)benzoate → 3,5-Bis(methoxymethoxy)benzylalcohol

HRID 1798077노트

반응식

HRID 1798077 반응식
C[O:2][C:3](=O)[C:4]1[CH:9]=[C:8]([O:10][CH2:11][O:12][CH3:13])[CH:7]=[C:6]([O:14][CH2:15][O:16][CH3:17])[CH:5]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>CCOCC>[CH3:13][O:12][CH2:11][O:10][C:8]1[CH:9]=[C:4]([CH2:3][OH:2])[CH:5]=[C:6]([O:14][CH2:15][O:16][CH3:17])[CH:7]=1

참가 물질

4

반응물 2

HCID 10106435Methyl 3,5-bis(methoxymethoxy)benzoateHCID 21226445Aluminium lithium hydride

생성물 1

HCID 104437513,5-Bis(methoxymethoxy)benzylalcohol수율 93%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

실험 절차

A solution of 3,5-bis-methoxymethoxybenzoic acid methyl ester (11.1 g, 43.3 mmol) in Et2O (150 mL) was treated with LiAlH4 (2.46 g, 65.0 mmol) at 0° C. The suspension was stirred at room temperature for 1 h. The reaction mixture was slowly quenched by water and extracted with ethyl acetate. The organic phase was separated, dried (Na2SO4), and concentrated. The residue was purified by flash column chromatography (silica, hexanes/ethyl acetate=2:3) to afford the title compound (9.16 g, 93%). 1H NMR (300 MHz, CDCl3) δ 6.71 (s, 1H), 6.70 (s, 1H), 6.64 (s, 1H), 5.15 (s, 4H), 4.62 (d, J=6.0 Hz, 2H), 3.47 (s, 6H), 1.93 (t, 1H).

후처리

  1. customThe reaction mixture was slowly quenched by water
  2. extractionextracted with ethyl acetate
  3. customThe organic phase was separated
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customThe residue was purified by flash column chromatography (silica, hexanes/ethyl acetate=2:3)

출처 및 근거

ORD 기록
ord-cd724ba28c784d8e8fa56f96a9acb67e
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08343944B2

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