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

HRID 1906967ノート

反応式

HRID 1906967 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 5943Carbon Tetrachloride溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-57bfe96629a0401f92bccc52d2452d5e
出典データセット
uspto-grants-1987_03
特許番号
US04654371

反応ノート

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