Methanol → 5-(Methoxycarbonyl)-2-methylbenzoic acid

HRID 397238

反応式

HRID 397238 の反応式
[CH3:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[C:11]([OH:13])=[O:12].S(Cl)(Cl)=O.N1C=CC=C[CH:19]=1.CO>CN(C=O)C.C(Cl)(Cl)(Cl)Cl>[CH3:19][O:7][C:6](=[O:8])[C:5]1[CH:9]=[CH:10][C:2]([CH3:1])=[C:3]([C:11]([OH:13])=[O:12])[CH:4]=1

参加物

7

反応物 4

HCID 887MethanolHCID 1049PyridineHCID 24386Thionyl ChlorideHCID 5957504-Methylbenzene-1,3-dicarboxylic acid

生成物 1

HCID 229994865-(Methoxycarbonyl)-2-methylbenzoic acid

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide触媒HCID 5943Carbon Tetrachloride溶媒

実験手順

A mixture of compound (2) (2.83 g, 15.71 mmol), thionyl chloride (50 ml) and DMF (3 drops) was heated at reflux for 2 hours. After cooling to room temperature, excess thionyl chloride was removed under reduced pressure (rotary evaporator). The dark oil which was obtained was dissolved in carbon tetrachloride (30 ml), treated with pyridine (1 ml, 12.43 mmol) and methanol (20 ml) and stirred at ambient temperature for 2 hours. The solvents were evaporated and the residue purified by flash chromatography: silica, hexane/EtOAc (9:1).

後処理

  1. temperaturewas heated
  2. temperatureat reflux for 2 hours
  3. customexcess thionyl chloride was removed under reduced pressure (rotary evaporator)
  4. customThe dark oil which was obtained
  5. customThe solvents were evaporated
  6. customthe residue purified by flash chromatography

出典と根拠

ORDレコード
ord-3c7986863cd943adb62352da01f11da9
出典データセット
uspto-grants-2003_08
特許番号
US06610269B1

関連ノート

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