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

HRID 263048

反応式

HRID 263048 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.C(O)C(O)CC>C1C=CC=CC=1>[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 2631-ButanolHCID 6101p-Toluenesulfonic acidHCID 114291,2-ButanediolHCID 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 241Benzene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 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-butanediol. 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 extract 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-8ebaba8887c245faa812883ab0727a29
出典データセット
uspto-grants-1979_05
特許番号
US04156008

関連ノート

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