Methanol → Methyl 3,4-Dihydroxy-2-methylbenzoate

HRID 2262413ノート

反応式

HRID 2262413 の反応式
[OH:1][C:2]1[C:3]([CH3:12])=[C:4]([CH:8]=[CH:9][C:10]=1[OH:11])[C:5]([OH:7])=[O:6].S(=O)(=O)(O)O.[CH3:18]O>>[CH3:18][O:6][C:5](=[O:7])[C:4]1[CH:8]=[CH:9][C:10]([OH:11])=[C:2]([OH:1])[C:3]=1[CH3:12]

参加物

4

反応物 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 104420733,4-Dihydroxy-2-methylbenzoic acid

生成物 1

HCID 59016598Methyl 3,4-Dihydroxy-2-methylbenzoate収率 83%

実験手順

To a round bottom flask equipped with magnetic stirring and a reflux condenser was added 3,4-dihydroxy-2-methylbenzoic acid (23.3 g, 139 mmol), methanol (139 mL), and concentrated sulfuric acid (0.77 mL, 13.9 mmol). This mixture was heated to reflux for 18 hours. The reaction was cooled to room temperature and the methanol evaporated. The residue was taken up in ether and washed once with saturated sodium bicarbonate solution, once with saturated sodium chloride solution, dried over sodium sulfate, filtered and evaporated to give a brown solid, methyl-3,4-dihydroxy-2-methylbenzoate, (20.9 g, 114 mmol) in 83% yield. 1H-NMR (300 MHz, CD3COCD3) δ (ppm): 2.47 (s, 3H), 3.79 (s, 3H), 6.78 (d, 1H), 7.46 (d, 1H); TLC: Rf=0.54 (1:1 ethyl acetate/hexane).

後処理

  1. customTo a round bottom flask equipped
  2. temperatureThis mixture was heated
  3. temperatureto reflux for 18 hours
  4. customthe methanol evaporated
  5. washwashed once with saturated sodium bicarbonate solution, once with saturated sodium chloride solution
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated

出典と根拠

ORDレコード
ord-3ed24f259143488c8aa89c195c6ef5d7
出典データセット
uspto-grants-2010_12
特許番号
US07851220B2

反応ノート

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