1,3-Propanediol → 2-(3-Ethyl-4-nitrophenyl)-2-phenyl-1,3-dioxane

HRID 2095232ノート

反応式

HRID 2095232 の反応式
[CH2:1]([C:3]1[CH:4]=[C:5]([CH:14]=[CH:15][C:16]=1[N+:17]([O-:19])=[O:18])[C:6]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:7])[CH3:2].[CH2:20](O)[CH2:21][CH2:22][OH:23]>C1(C)C=CC=CC=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH2:1]([C:3]1[CH:4]=[C:5]([C:6]2([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)[O:23][CH2:22][CH2:21][CH2:20][O:7]2)[CH:14]=[CH:15][C:16]=1[N+:17]([O-:19])=[O:18])[CH3:2]

参加物

5

反応物 2

HCID 104421,3-PropanediolHCID 533755813-Ethyl-4-nitro-benzophenone

生成物 1

HCID 593862972-(3-Ethyl-4-nitrophenyl)-2-phenyl-1,3-dioxane収率 91.8%

試薬・触媒・溶媒 2

HCID 521998p-Toluenesulfonic acid monohydrate触媒HCID 1140Toluene溶媒

実験手順

A suspension of 3-ethyl-4-nitro-benzophenone (11f) (20.0 g, 78.4 mmol), 1,3-propandiol (7.15 g, 94.0 mmol), p-toluenesulfonic acid monohydrate (50 mg) in toluene (300 mL) was refluxed using a Dean-Stark-trap for 24 hours. The Dean-Stark-trap was then replaced by a Soxhlet-extractor filled with molecular sieve and the mixture was refluxed for an additional 48 hours to achieve complete conversion. The reaction mixture was then cooled to ambient temperature, washed with an aqueous, saturated solution of NaHCO3 and concentrated in vacuo until crystallization started. The suspension was cooled for 0.5 hours in an ice bath and after which the crystalline product was filtered, washed with a small volume of hexane and air dried to give 22.48 g (72 mmol, 91.5%) compound 17 as yellow crystals.

後処理

  1. temperaturewas refluxed
  2. customfor 24 hours
  3. additionfilled with molecular sieve
  4. temperaturethe mixture was refluxed for an additional 48 hours
  5. washwashed with an aqueous, saturated solution of NaHCO3
  6. concentrationconcentrated in vacuo until crystallization
  7. temperatureThe suspension was cooled for 0.5 hours in an ice bath
  8. filtrationafter which the crystalline product was filtered
  9. washwashed with a small volume of hexane and air
  10. customdried

出典と根拠

ORDレコード
ord-29d66b647aaa4fc3aec59f84b1de373e
出典データセット
uspto-grants-2013_05
特許番号
US08445734B2

反応ノート

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