Phenol → alpha-Hydroxy-beta-Phenoxy-N-(1-Methylethyl)Benzenepropanamide

HRID 435494

反応式

HRID 435494 の反応式
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Na].C1OCCOCCOCCOCCOCCOC1.[CH3:27][CH:28]([NH:30][C:31]([CH:33]1[CH:35]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[O:34]1)=[O:32])[CH3:29]>C[O-].[Na+].CO.CO.C(#N)C.O>[OH:34][CH:33]([CH:35]([O:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1)[C:31]([NH:30][CH:28]([CH3:27])[CH3:29])=[O:32]

参加物

9

反応物 4

HCID 996PhenolHCID 2855718-Crown-6HCID 5360545SodiumHCID 13041334N-(1-methylethyl)-3-phenyl-2-oxiranecarboxamide

生成物 1

HCID 13041337alpha-Hydroxy-beta-Phenoxy-N-(1-Methylethyl)Benzenepropanamide

試薬・触媒・溶媒 4

HCID 887Methanol溶媒HCID 962Water溶媒HCID 6342Acetonitrile溶媒HCID 23694274Sodium methanolate methanol溶媒

実験手順

Phenol (3.0 g.) was converted into its sodium salt by dissolving in a freshly prepared sodium methoxide-methanol solution (0.7 g. of metallic sodium in 50 ml. of absolute methanol), and subsequent evaporation of the excess methanol under reduced pressure on a rotary evaporator. The solid residue was dissolved in acetonitrile (250 ml.) by stirring with 18-crown-6 (0.9 g.) for 30 minutes at room temperature. N-(1-methylethyl)-3-phenyl-2-oxiranecarboxamide (6.16 g.) was added to the solution, and the resulting mixture was heated under reflux for 6 hours. After cooling to room temperature, it was filtered. The filtrate was evaporated on a rotary evaporator under reduced pressure to give a resinous material. Water (ca. 200 ml.) was added to the residue, and allowed to stand at room temperature. The white precipitate thus separated was collected on a filter and washed with water. The filter residue was dried in air, then recrystallized from ethanol, giving 2.5 g. of product, m.p. 166°-168°.

後処理

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 6 hours
  3. filtrationit was filtered
  4. customThe filtrate was evaporated on a rotary evaporator under reduced pressure
  5. customto give a resinous material
  6. customto stand at room temperature
  7. customThe white precipitate thus separated
  8. customwas collected on
  9. filtrationa filter
  10. washwashed with water
  11. customThe filter residue was dried in air
  12. customrecrystallized from ethanol
  13. customgiving 2.5 g

出典と根拠

ORDレコード
ord-2eff274049404294a3eeba4635cbf2a2
出典データセット
uspto-grants-1983_08
特許番号
US04401832

関連ノート

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