Benzene → 1,3-Dioxolane, 2-(bromomethyl)-2-(2-naphthalenyl)-

HRID 1679128

反応式

HRID 1679128 の反応式
[Br:1][CH2:2][C:3]([C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=1)=[O:4].[CH2:15]([OH:19])[CH2:16]CC.CC1C=CC(S(O)(=O)=O)=CC=1.C1C=CC=CC=1>C(O)CO>[Br:1][CH2:2][C:3]1([C:5]2[CH:14]=[CH:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[CH:6]=2)[O:19][CH2:15][CH2:16][O:4]1

参加物

6

反応物 4

HCID 241BenzeneHCID 2631-ButanolHCID 6101p-Toluenesulfonic acidHCID 691792-Bromo-2'-acetonaphthone

生成物 1

HCID 6079971,3-Dioxolane, 2-(bromomethyl)-2-(2-naphthalenyl)-

試薬・触媒・溶媒 1

HCID 174Ethylene Glycol溶媒

実験手順

To a stirred solution of 74.4 parts of 2-bromo-1-(2-naphthalenyl)-1-ethanone in 240 parts of a butanol are added successively 3 parts of 4-methylbenzenesulfonic acid and 270 parts of benzene. Then there are added dropwise 28 parts of 1,2-ethanediol. Upon completion, stirring is continued overnight at reflux temperature. The reaction mixture is evaporated. The residue is dissolved in 2,2'-oxybispropane and the solution is stirred with a diluted sodium hydroxide solution. The layers are separated and the aqueous phase is extracted with 2,2'-oxybispropane. The extra ct is neutralized with water, dried, filtered and evaporated. The oily residue is crystallized from methanol. The product is filtered off and recrystallized from methanol, yielding 41 parts of 2-(bromomethyl)-2-(2-naphthalenyl)-1,3-dioxolane; mp. 64° C.

後処理

  1. temperatureat reflux temperature
  2. customThe reaction mixture is evaporated
  3. dissolutionThe residue is dissolved in 2,2'-oxybispropane
  4. stirringthe solution is stirred with a diluted sodium hydroxide solution
  5. customThe layers are separated
  6. extractionthe aqueous phase is extracted with 2,2'-oxybispropane
  7. customdried
  8. filtrationfiltered
  9. customevaporated
  10. customThe oily residue is crystallized from methanol
  11. filtrationThe product is filtered off
  12. customrecrystallized from methanol

出典と根拠

ORDレコード
ord-4c3488e9e9b24c9492349b3290d13e59
出典データセット
uspto-grants-1978_03
特許番号
US04079062

関連ノート

読み込み中…