Acetone → Methyl 2-methoxy-5-methylbenzoate

HRID 128774

反応式

HRID 128774 の反応式
[CH3:1][C:2]1[CH:10]=[C:6]([C:7]([OH:9])=O)[C:5]([OH:11])=[CH:4][CH:3]=1.[C:12](=O)([O-])[O-].[K+].[K+].CC(C)=O.S([O:27][CH3:28])(OC)(=O)=O>O>[CH3:12][O:11][C:5]1[CH:4]=[CH:3][C:2]([CH3:1])=[CH:10][C:6]=1[C:7]([O:27][CH3:28])=[O:9]

参加物

6

反応物 4

HCID 180AcetoneHCID 6497Dimethyl Sulfate2 回HCID 69735-Methylsalicylic acidHCID 11430Potassium Carbonate

生成物 1

HCID 10241396Methyl 2-methoxy-5-methylbenzoate収率 91.1%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

5.07 g (33.32×10-3 mol) of 5-methylsalicylic acid and 22.33 g (161.6×10-3 mol) of anhydrous potassium carbonate are introduced into a 250-cm3 two-necked flask. 175 cm3 of anhydrous acetone are added under an inert atmosphere. The reaction mixture is stirred, 7.25 cm3 (76.62×10-3 mol) of dimethyl sulfate are added with a syringe and the mixture is brought to reflux for 6 h. Hydrolysis of the dimethyl sulfate is performed by adding 5 cm3 of water. After filtration and evaporation of the solvent, the residue is taken up with dichloromethane, dried over MgSO4 and then evaporated to dryness. The crude product is purified by chromatography on a silica column (eluent: CH2Cl2) to give 5.47 g (30.36×10-3 mol) of the expected ester, equivalent to a 91% yield.

後処理

  1. temperatureto reflux for 6 h
  2. filtrationAfter filtration and evaporation of the solvent
  3. dry with materialdried over MgSO4
  4. customevaporated to dryness
  5. customThe crude product is purified by chromatography on a silica column (eluent: CH2Cl2)

出典と根拠

ORDレコード
ord-551661e6d5f1435cb5a86af102a228b2
出典データセット
uspto-grants-1995_11
特許番号
US05464872

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