p-Toluenesulfonic acid → 2-(Bromomethyl)-4-[(4-chlorophenoxy)methyl]-2-(4-chlorophenyl)-1,3-dioxolane

HRID 1578433ノート

反応式

HRID 1578433 の反応式
[Br:1][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][CH:6]=1)=[O:4].[Cl:12][C:13]1[CH:24]=[CH:23][C:16]([O:17][CH2:18][CH:19]([OH:22])[CH2:20]O)=[CH:15][CH:14]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[Br:1][CH2:2][C:3]1([C:5]2[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][CH:6]=2)[O:22][CH:19]([CH2:18][O:17][C:16]2[CH:15]=[CH:14][C:13]([Cl:12])=[CH:24][CH:23]=2)[CH2:20][O:4]1

参加物

5

反応物 3

HCID 6101p-Toluenesulfonic acidHCID 7697ChlorphenesinHCID 68303p-Chlorophenacyl bromide

生成物 1

HCID 203326492-(Bromomethyl)-4-[(4-chlorophenoxy)methyl]-2-(4-chlorophenyl)-1,3-dioxolane

試薬・触媒・溶媒 1

HCID 241Benzene溶媒

実験手順

A mixture of 11.7 parts of 2-bromo-4'-chloroacetophenone, 12.2 parts of 1-(p-chlorophenoxy)-2,3-propanediol, 3 parts of p-toluenesulfonic acid and 240 parts of benzene is stirred and refluxed for 20 hours in a four-necked round-bottom flask equipped with a watertrap. The benzene solution is washed successively with a diluted sodium hydroxide solution and with water. The solvent is removed in vacuo. The residue is triturated in methanol. The precipitated product is filtered off (methanol filtrate is set aside) and crystallized from toluene, yielding A-2-(bromomethyl-4-(p-chlorophenoxymethyl)-2-(p-chlorophenyl)-1,3-dioxolane; m.p. 165°C.

後処理

  1. temperaturerefluxed for 20 hours in a four-necked round-bottom flask
  2. customequipped with a watertrap
  3. washThe benzene solution is washed successively with a diluted sodium hydroxide solution and with water
  4. customThe solvent is removed in vacuo
  5. customThe residue is triturated in methanol
  6. filtrationThe precipitated product is filtered off (methanol filtrate
  7. customcrystallized from toluene

出典と根拠

ORDレコード
ord-ed4f67585ce84caeb44a058025c132e3
出典データセット
uspto-grants-1976_02
特許番号
US03936470

反応ノート

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