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

HRID 1798077ノート

反応式

HRID 1798077 の反応式
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

参加物

4

反応物 2

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

生成物 1

HCID 104437513,5-Bis(methoxymethoxy)benzylalcohol収率 93%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-cd724ba28c784d8e8fa56f96a9acb67e
出典データセット
uspto-grants-2013_01
特許番号
US08343944B2

反応ノート

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