Dimethyl Sulfate → Methyl 4-methoxysalicylate

HRID 256337

反応式

HRID 256337 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([OH:12])[C:6](=[CH:10][CH:11]=1)[C:7]([OH:9])=[O:8].[C:13](=O)(O)[O-].[Na+].S(OC)(OC)(=O)=O>CC(C)=O.CCOCC.C1(C)C=CC=CC=1>[CH3:13][O:8][C:7](=[O:9])[C:6]1[C:5](=[CH:4][C:3]([O:2][CH3:1])=[CH:11][CH:10]=1)[OH:12]

参加物

7

反応物 3

HCID 6497Dimethyl SulfateHCID 752314-Methoxysalicylic AcidHCID 516892Sodium Bicarbonate

生成物 1

HCID 79523Methyl 4-methoxysalicylate収率 98,858.797%

試薬・触媒・溶媒 3

HCID 180Acetone溶媒HCID 1140Toluene溶媒HCID 3283Diethyl Ether溶媒

実験手順

A mixture of 4-methoxysalicylic acid (Aldrich) (178.1 g, 1.06 mmole) sodium bicarbonate (89 g, 1.06 mole), and dimethyl sulfate (133.6 g, 1.06 mole) in acetone (2 l) is refluxed with stirring under nitrogen for 20 hours. The mixture is cooled, filtered, and the acetone is removed under reduced pressure to yield an oily residue. The residue is taken up in ether (1.8 l) and toluene (0.50 l). The extracts are washed with sodium bicarbonate solution, water, dried over sodium sulfate, and concentrated to give a syrup (190.9 g). Recrystallization from hexane gives 172.7 g (89.5%) of analytically pure solid, mp 49°-50° C.

後処理

  1. temperatureis refluxed
  2. temperatureThe mixture is cooled
  3. filtrationfiltered
  4. customthe acetone is removed under reduced pressure
  5. customto yield an oily residue
  6. washThe extracts are washed with sodium bicarbonate solution, water
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-f7f85d8a445d4379b1ab9d2dff21c91b
出典データセット
uspto-grants-1987_10
特許番号
US04703053

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