p-Toluenesulfonic acid → 4-Methoxy-2,2-dimethyl-1,3-benzodioxole

HRID 1057947

반응식

HRID 1057947 반응식
[CH3:1][O:2][C:3]1[CH:9]=[CH:8][CH:7]=[C:5]([OH:6])[C:4]=1[OH:10].S([C:15]1[CH:21]=CC(C)=C[CH:16]=1)(O)(=O)=O.[OH-].[Na+]>C1C=CC=CC=1>[CH3:1][O:2][C:3]1[C:4]2[O:10][C:15]([CH3:21])([CH3:16])[O:6][C:5]=2[CH:7]=[CH:8][CH:9]=1

참가 물질

5

반응물 3

HCID 6101p-Toluenesulfonic acidHCID 136223-MethoxycatecholHCID 14798Sodium Hydroxide

생성물 1

HCID 150610944-Methoxy-2,2-dimethyl-1,3-benzodioxole

시약·촉매·용매 1

HCID 241Benzene용매

실험 절차

3-methoxycatechol (25 g) was dissolved in benzene, mixed with dimethoxyacetal (35 ml) and a catalytic amount of tosylic acid, and then, heat-refluxed for 6 hours. The resultant was allowed to stand for cooling, alkalified by adding an aqueous sodium hydroxide solution, and extracted with ether. The organic layer was washed with a saturated aqueous sodium chloride solution, dried over manganese sulfate, and evaporated under reduced pressure for removing the solvent. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=99/1) to give Compound IIbv-a (19.4 g, 60.5%) as a white solid.

후처리

  1. temperaturefor cooling
  2. extractionextracted with ether
  3. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  4. dry with materialdried over manganese sulfate
  5. customevaporated under reduced pressure
  6. customfor removing the solvent
  7. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=99/1)
  8. customto give Compound IIbv-a (19.4 g, 60.5%) as a white solid

출처 및 근거

ORD 기록
ord-6333eb2aab974270b8b7deba206c7a2b
출처 데이터셋
uspto-grants-2003_02
특허 번호
US06514996B2

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