p-Toluenesulfonic acid monohydrate → Methyl 4-cyano-2-methoxybenzoate

HRID 909104ノート

反応式

HRID 909104 の反応式
[C:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[C:5]([O:12][CH3:13])[CH:4]=1)#[N:2].O.[C:15]1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[CH3:15][O:8][C:7](=[O:9])[C:6]1[CH:10]=[CH:11][C:3]([C:1]#[N:2])=[CH:4][C:5]=1[O:12][CH3:13]

参加物

4

反応物 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 151660044-Cyano-2-methoxybenzoic acid

生成物 1

HCID 57426183Methyl 4-cyano-2-methoxybenzoate収率 367.6%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a mixture of 4-cyano-2-methoxybenzoic acid (1.00 g, 5.648 mmol, Biogene) in methanol (15.0 mL) was added p-toluenesulfonic acid monohydrate (286 mg, 1.48 mmol, Aldrich) and it was heated to reflux under an argon atmosphere for 16 hrs. The solvent was removed and the reaction mixture was extracted with EtOAc, washed with saturated Na2CO3, water, and saturated NaCl. The organic phase was separated, dried over Na2SO4, filtered and concentrated to give 4-cyano-2-methoxy-benzoic acid methyl ester (1.04 g, 96.4%).

後処理

  1. temperaturewas heated
  2. temperatureto reflux under an argon atmosphere for 16 hrs
  3. customThe solvent was removed
  4. extractionthe reaction mixture was extracted with EtOAc
  5. washwashed with saturated Na2CO3, water, and saturated NaCl
  6. customThe organic phase was separated
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated

出典と根拠

ORDレコード
ord-0d3b7d81ef4b46ae93156d04e02dee91
出典データセット
uspto-grants-2011_09
特許番号
US08017607B2

反応ノート

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