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

HRID 1057941

反応式

HRID 1057941 の反応式
[CH3:1][O:2][C:3]1[CH:9]=[CH:8][CH:7]=[C:5]([OH:6])[C:4]=1[OH:10].[C:11]1(C)[CH:16]=CC(S(O)(=O)=O)=C[CH:12]=1.[OH-].[Na+]>C1C=CC=CC=1>[CH3:1][O:2][C:3]1[C:4]2[O:10][C:11]([CH3:16])([CH3:12])[O:6][C:5]=2[CH:7]=[CH:8][CH:9]=1

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 241Benzene溶媒

実験手順

3-Methoxycatechol (25 g) was dissolved in benzene, and dimethoxyacetal (35 ml) and a catalytic amount of p-toluenesulfonic acid were added thereto, followed by heating at reflux for 6 hours. After being allowed to stand for cooling, the mixture was adjusted to alkaline with an aqueous solution of sodium hydroxide, followed by extraction with ether. The organic layer was washed with a saturated saline and dried over magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=99/1) to give Compound IIbk-a (19.4 g, 60.5%) as a white solid.

後処理

  1. temperatureby heating
  2. temperatureat reflux for 6 hours
  3. temperaturefor cooling
  4. extractionfollowed by extraction with ether
  5. washThe organic layer was washed with a saturated saline
  6. dry with materialdried over magnesium sulfate
  7. distillationthe solvent was distilled off under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=99/1)
  9. customto give Compound IIbk-a (19.4 g, 60.5%) as a white solid

出典と根拠

ORDレコード
ord-b56b9681518f4d3ebb66dfcc047e363d
出典データセット
uspto-grants-2003_02
特許番号
US06514996B2

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