Methanol → Methyl 3-hydroxy-4-methoxybenzoate

HRID 253266

反応式

HRID 253266 の反応式
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[C:5]([OH:7])=[O:6].S(=O)(=O)(O)O.[CH3:18]O>>[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[C:5]([O:7][CH3:18])=[O:6]

参加物

4

反応物 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 12575Isovanillic Acid

生成物 1

HCID 4056967Methyl 3-hydroxy-4-methoxybenzoate収率 100%

実験手順

To a suspension of 3-hydroxy-4-(methyloxy)benzoic acid (25 g, 149 mmol.) in methanol (200 mL) was added concentrated sulfuric acid (1 mL) and the mixture was brought to reflux over 18 hours. The resulting homogeneous solution was cooled to room temperature, concentrated in vacuo and the residual oil taken into ethyl acetate (300 mL). The solution was washed once with water, saturated aqueous sodium hydrogencarbonate then brine and dried over anhydrous magnesium sulfate. Filtration and concentration gave methyl 3-hydroxy-4-(methyloxy)benzoate (27 g, 100% yield) as an oil. 1H NMR (400 MHz, CDCl3): 7.59 (dd, 1H), 7.57 (d, 1H), 6.85 (d, 1H), 5.72 (s, 1H), 3.93 (s, 3H), 3.87 (s, 3H).

後処理

  1. temperatureto reflux over 18 hours
  2. concentrationconcentrated in vacuo
  3. washThe solution was washed once with water, saturated aqueous sodium hydrogencarbonate
  4. dry with materialbrine and dried over anhydrous magnesium sulfate
  5. filtrationFiltration and concentration

出典と根拠

ORDレコード
ord-1644616bda074dc38c3b442a22c41c54
出典データセット
uspto-grants-2011_01
特許番号
US07872014B2

関連ノート

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