Vanillin → 4-(Difluoromethoxy)-3-methoxybenzaldehyde

HRID 727381ノート

反応式

HRID 727381 の反応式
Cl[CH:2]([F:4])[F:3].[O:5]=[CH:6][C:7]1[CH:15]=[CH:14][C:12]([OH:13])=[C:9]([O:10][CH3:11])[CH:8]=1.[OH-].[Na+]>[Cl-].C([N+](C)(C)C)C1C=CC=CC=1.O1CCOCC1>[F:3][CH:2]([F:4])[O:13][C:12]1[CH:14]=[CH:15][C:7]([CH:6]=[O:5])=[CH:8][C:9]=1[O:10][CH3:11]

参加物

6

反応物 3

HCID 1183VanillinHCID 6372ChlorodifluoromethaneHCID 14798Sodium Hydroxide

生成物 1

HCID 31612494-(Difluoromethoxy)-3-methoxybenzaldehyde

試薬・触媒・溶媒 2

HCID 5963Benzyltrimethylammonium chloride触媒HCID 312751,4-Dioxane溶媒

実験手順

Chlorodifluoromethane is introduced into a mixture of 200 g of vanillin, 6.7 g of benzyltrimethylammonium chloride, 314 g of 50% strength sodium hydroxide solution and 2 liters of dioxane with vigorous stirring for about 2 h. The mixture is then partitioned between ice water and ethyl acetate, the organic phase is separated off, the aqueous phase is extracted twice by stirring with ethyl acetate, and the combined organic phases are dried over magnesium sulphate and concentrated in vacuo. To remove unreacted vanillin, the oil is chromatographed on neutral silica gel using toluene. After evaporating the eluate, 249 g of 4-difluoromethoxy-3-methoxybenzaldehyde are obtained as an oil.

後処理

  1. customThe mixture is then partitioned between ice water and ethyl acetate
  2. customthe organic phase is separated off
  3. extractionthe aqueous phase is extracted twice
  4. stirringby stirring with ethyl acetate
  5. dry with materialthe combined organic phases are dried over magnesium sulphate
  6. concentrationconcentrated in vacuo
  7. customTo remove unreacted vanillin
  8. customthe oil is chromatographed on neutral silica gel
  9. customAfter evaporating the eluate, 249 g of 4-difluoromethoxy-3-methoxybenzaldehyde
  10. customare obtained as an oil

出典と根拠

ORDレコード
ord-213cd97d73504a0ab088129ab9fe97dd
出典データセット
uspto-grants-1998_01
特許番号
US05712298

反応ノート

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