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Trifluoroacetic acid → 1-Acetoxy-1-(3-chlorophenyl)-2-(2-hydroxyethoxy)ethane

HRID 862503
ノート
印刷プレビュー

反応式

HRID 862503 の反応式
[C:1]([O:4][CH:5]([C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[CH:16]=1)[CH2:6][O:7][CH2:8][CH2:9][O:10]C(C)(C)C)(=[O:3])[CH3:2].FC(F)(F)C(O)=O.C(=O)([O-])O.[Na+]>C(Cl)Cl.C(O)C.O>[C:1]([O:4][CH:5]([C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[CH:16]=1)[CH2:6][O:7][CH2:8][CH2:9][OH:10])(=[O:3])[CH3:2]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium Bicarbonate2 回HCID 53824717Acetoxy-1-(3-chlorophenyl)-2-(2-tertbutoxyethoxy)ethane

生成物 1

HCID 537909691-Acetoxy-1-(3-chlorophenyl)-2-(2-hydroxyethoxy)ethane収率 59%

試薬・触媒・溶媒 3

HCID 702Ethanol溶媒
HCID 962
Water
溶媒
HCID 6344Dichloromethane溶媒

実験手順

40.0 g of 1-acetoxy-l-(3-chlorophenyl)-2-(2-tert-butoxyethoxy)ethane was dissolved in 40 ml of methylene chloride. To the solution was added 80 ml of trifluoroacetic acid with ice cooling. The mixture was stirred for 12 hours at room temperature. After the completion of the reaction, the solvent was removed by distillation under reduced pressure. The residue was mixed with 100 ml of toluene. The solvent was further removed by distillation under reduced pressure. The residue thus obtained was dissolved in a mixture of 90 ml of ethanol and 10 ml of water. To the solution was added 10.7 g of sodium hydrogencarbonate at room temperature. The mixture was adjusted to pH 6-7 with a saturated aqueous sodium hydrogencarbonate solution, and then concentrated to about a half volume under reduced pressure. To the concentrate was added 100 ml of ethyl acetate. The organic layer was separated. The aqueous layer was extracted with 50 ml of ethyl acetate. The extract was combined with the previously separated organic layer. The combined organic layer was washed with a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The residue was purified by column chromatography (eluant: toluene/ethyl acetate=3/1) to obtain 19.4 g of oily 1-acetoxy-1-(3-chlorophenyl)-2-(2-hydroxyethoxy)ethane.

後処理

  1. customAfter the completion of the reaction
  2. customthe solvent was removed by distillation under reduced pressure
  3. additionThe residue was mixed with 100 ml of toluene
  4. customThe solvent was further removed by distillation under reduced pressure
  5. customThe residue thus obtained
  6. concentrationconcentrated to about a half volume under reduced pressure
  7. additionTo the concentrate was added 100 ml of ethyl acetate
  8. customThe organic layer was separated
  9. extractionThe aqueous layer was extracted with 50 ml of ethyl acetate
  10. washThe combined organic layer was washed with a saturated aqueous sodium chloride solution
  11. dry with materialdried over anhydrous magnesium sulfate
  12. customThe solvent was removed by distillation under reduced pressure
  13. customThe residue was purified by column chromatography (eluant: toluene/ethyl acetate=3/1)

出典と根拠

ORDレコード
ord-4825da9cfc054879a0a528923d47ed99
出典データセット
uspto-grants-1998_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05719150

反応ノート

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