Dichloromethane → Benzaldehyde, 2-methoxy-5-nitro-

HRID 647205

反応式

HRID 647205 の反応式
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].C(Cl)Cl.[CH3:15][O:16]C(Cl)Cl>O.[Ti](Cl)(Cl)(Cl)Cl>[CH3:11][O:10][C:7]1[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][C:8]=1[CH:15]=[O:16]

参加物

6

反応物 3

HCID 6344DichloromethaneHCID 74854-NitroanisoleHCID 21004Methane, dichloromethoxy-

生成物 1

HCID 90685Benzaldehyde, 2-methoxy-5-nitro-

試薬・触媒・溶媒 2

HCID 24193Titanium Tetrachloride触媒HCID 962Water溶媒

実験手順

p-Nitroanisole (25 g., 0.163 mole) was dissolved in 400 ml. of methylene chloride and cooled to 10° C. Titanium tetrachloride (61.8 g., 36 ml., 0.326 mole) was added, followed by 1,1-dichloromethyl methyl ether added over 2 minutes. The mixture was warmed to room temperature and stirred for 42 hours. The reaction mixture was diluted with 1 liter of ice and water and extracted with three 500 ml. portions of methylene chloride. The organic extracts were combined, washed with two portions of water and one of brine, dried over anhydrous magnesium sulfate, filtered and concentrated to an oil (20 g.). The oil was chromatographed on 600 g. silica gel, using 2:1 methylene chloride:hexane as eluant, collecting 15 ml. fractions, and monitoring by tlc. Clean product fractions 79-185 were combined and evaporated to yield 2-methoxy-5-nitrobenzaldehyde (3.8 g.; m.p. 87-89, literature m.p. 89°-90°).

後処理

  1. additionadded over 2 minutes
  2. extractionextracted with three 500 ml
  3. washwashed with two portions of water and one of brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to an oil (20 g.)
  7. customThe oil was chromatographed on 600 g
  8. customhexane as eluant, collecting 15 ml
  9. customevaporated

出典と根拠

ORDレコード
ord-9e31f41c867d43748c011d9187f98c95
出典データセット
uspto-grants-1983_10
特許番号
US04407811

関連ノート

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