Benzoyl Peroxide → Methyl 4-(bromomethyl)-2-methylbenzoate

HRID 1906967

Reaktionsgleichung

Reaktionsgleichung von HRID 1906967
[Br:1]N1C(=O)CCC1=O.[CH3:9][C:10]1[CH:19]=[C:18]([CH3:20])[CH:17]=[CH:16][C:11]=1[C:12]([O:14][CH3:15])=[O:13].C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.CC1C=CC=C2C=1COC2=O>C(Cl)(Cl)(Cl)Cl>[C:12]([C:11]1[CH:16]=[CH:17][C:18]([CH2:20][Br:1])=[CH:19][C:10]=1[CH3:9])([O:14][CH3:15])=[O:13]

Komponenten

6

Edukt 4

HCID 7187Benzoyl PeroxideHCID 32031Methyl 2,4-dimethylbenzoateHCID 67184N-bromobutanimideHCID 6387554-methyl-2-benzofuran-1(3H)-one

Produkt 1

HCID 19372658Methyl 4-(bromomethyl)-2-methylbenzoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 5943Carbon TetrachlorideLösungsmittel

Versuchsvorschrift

N-Bromosuccinimide (44.9 g) was added to a solution of methyl 2,4-dimethylbenzoate (41.36 g) in carbon tetrachloride containing a trace of dibenzoyl peroxide. The mixture was heated under reflux until no orange colour persisted then cooled, filtered and the filtrate evaporated to leave an oil. This was distilled until ~16 g distillate bp 98°-140°/0.8-5 mm (starting material ) had been collected. The residue was then heated at atmospheric pressure until no more methyl bromide was evolved, to give a mixture of the title compound and 4-methylphthalide. Addition of hot petrol and filtration from the phthalide gave after evaporation the title compound. τ (CDCl3) 7.48 (3H, s), 6.21 (3H, s), 5.65 (2H, s), 2.6-2.93 (2H, m), 2.18 (1H, d, J=8 Hz).

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureunder reflux until no orange colour
  3. temperaturepersisted then cooled
  4. filtrationfiltered
  5. customthe filtrate evaporated
  6. customto leave an oil
  7. distillationThis was distilled until ~16 g distillate bp 98°-140°/0.8-5 mm (starting material )
  8. customhad been collected
  9. temperatureThe residue was then heated at atmospheric pressure until no more methyl bromide
  10. customto give

Quellen und Nachweise

ORD-Eintrag
ord-57bfe96629a0401f92bccc52d2452d5e
Quelldatensatz
uspto-grants-1987_03
Patentnummer
US04654371

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