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

HRID 544333

반응식

HRID 544333 반응식
[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]

참가 물질

6

반응물 3

HCID 6344DichloromethaneHCID 74854-NitroanisoleHCID 21004Methane, dichloromethoxy-

생성물 1

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

시약·촉매·용매 2

HCID 24193Titanium Tetrachloride촉매HCID 962Water용매

실험 절차

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°).

후처리

  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

출처 및 근거

ORD 기록
ord-8283ee1424524e1590557897d80edd4d
출처 데이터셋
uspto-grants-1984_05
특허 번호
US04448971

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