Methyl 2-(bromomethyl)-3-nitrobenzoate → 4-Nitrophthalide

HRID 1247853Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1247853
BrC[C:3]1[C:12]([N+:13]([O-:15])=[O:14])=[CH:11][CH:10]=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6]>O1CCOCC1.O>[N+:13]([C:12]1[C:3]2[CH2:8][O:7][C:5](=[O:6])[C:4]=2[CH:9]=[CH:10][CH:11]=1)([O-:15])=[O:14]

Komponenten

4

Edukt 1

HCID 1487795Methyl 2-(bromomethyl)-3-nitrobenzoate

Produkt 1

HCID 12116924-NitrophthalideAusbeute 59,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A solution of 54.8 g of methyl 2-bromomethyl-3-nitrobenzoate in a mixture of 200 ml dioxane and 45 ml water was refluxed for 72 hours. The reaction solution was cooled and concentrated in vacuo. The resulting solid was slurried in water, collected, washed with water and dried. Recrystallization from 1-chlorobutane gave 21.4 g of 1,3-dihydro-4-nitrobenzo[c]furan-1-one, m.p. 133.5°-136°.

Aufarbeitung

  1. temperaturewas refluxed for 72 hours
  2. temperatureThe reaction solution was cooled
  3. concentrationconcentrated in vacuo
  4. customcollected
  5. washwashed with water
  6. customdried
  7. customRecrystallization from 1-chlorobutane

Quellen und Nachweise

ORD-Eintrag
ord-4f58b6c48f7d4041a96c481fcd8f1d39
Quelldatensatz
uspto-grants-1985_06
Patentnummer
US04521241

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