p-Toluenesulfonic acid → (E)-1-[3-(4-Chlorophenoxy)phenyl]buten-3-one

HRID 704813

反応式

HRID 704813 の反応式
[OH-:1].[Na+].[Cl:3][C:4]1[CH:18]=[CH:17][C:7]([O:8][C:9]2[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=2)[CH:12]=O)=[CH:6][CH:5]=1.[C:19]1([CH3:29])C=CC(S(O)(=O)=O)=C[CH:20]=1>CC(C)=O.C1(C)C=CC=CC=1>[Cl:3][C:4]1[CH:18]=[CH:17][C:7]([O:8][C:9]2[CH:10]=[C:11](/[CH:12]=[CH:20]/[C:19](=[O:1])[CH3:29])[CH:14]=[CH:15][CH:16]=2)=[CH:6][CH:5]=1

参加物

6

反応物 3

HCID 6101p-Toluenesulfonic acidHCID 14798Sodium HydroxideHCID 6160153-(4-Chlorophenoxy)benzaldehyde

生成物 1

HCID 20073366(E)-1-[3-(4-Chlorophenoxy)phenyl]buten-3-one

試薬・触媒・溶媒 2

HCID 180Acetone溶媒HCID 1140Toluene溶媒

実験手順

10 N aqu. NaOH (2 ml) was added to a solution of 3-(4-chlorophenoxy)-benzaldehyde (23.3 g, Aldrich) in acetone (150 ml) and stirred vigorously. After a few minutes' stirring, the temperature rose to 32° C. The mixture was left for 5 minutes and then poured into 2 M aqu. HCl (600 ml) and extracted with ether/pet. ether (1:1, 200 ml). The extract was washed with water and satd. aqu. NaCl, dried over MgSO4, and stripped to give the aldol product. The latter was taken up in toluene (300 ml), p-toluenesulphonic acid (1 g) was added, and the mixture heated for 1 hour. The mixture was then cooled, washed with satd. aqu. NaHCO3 and satd. aqu. NaCl, dried over MgSO4 and stripped. The residue was eluted through a slice gel column using methylene chloride/40-60 pet. ether (1:1, followed by 3:1) and the eluate stripped to give the desired product (19 g).

後処理

  1. stirringAfter a few minutes' stirring
  2. customrose to 32° C
  3. additionpoured into 2 M aqu
  4. extractionHCl (600 ml) and extracted with ether/pet. ether (1:1, 200 ml)
  5. washThe extract was washed with water and satd
  6. dry with materialNaCl, dried over MgSO4
  7. customto give the aldol product
  8. temperaturethe mixture heated for 1 hour
  9. temperatureThe mixture was then cooled
  10. washwashed with satd
  11. dry with materialNaCl, dried over MgSO4
  12. washThe residue was eluted through a slice gel column

出典と根拠

ORDレコード
ord-b20afd6f017c485282cb258baae5a590
出典データセット
uspto-grants-1991_01
特許番号
US04988733

関連ノート

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