Dimethyl Sulfate → Methyl 4-methoxysalicylate

HRID 256337

반응식

HRID 256337 반응식
[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]

참가 물질

7

반응물 3

HCID 6497Dimethyl SulfateHCID 752314-Methoxysalicylic AcidHCID 516892Sodium Bicarbonate

생성물 1

HCID 79523Methyl 4-methoxysalicylate수율 98,858.797%

시약·촉매·용매 3

HCID 180Acetone용매HCID 1140Toluene용매HCID 3283Diethyl Ether용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-f7f85d8a445d4379b1ab9d2dff21c91b
출처 데이터셋
uspto-grants-1987_10
특허 번호
US04703053

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