Acetic Anhydride → 4-Acetoxy stilbene

HRID 359338ノート

反応式

HRID 359338 の反応式
C(N(CC)CC)C.[OH:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]=[CH:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:11][CH:10]=1.[CH3:23][C:24](OCC1C2C(=CC=CC=2)C(COC(C)=O)=C2C=1C=CC=C2)=[O:25].C(OC(=O)C)(=O)C>C1COCC1>[C:24]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH:15]=[CH:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)=[CH:13][CH:14]=1)(=[O:25])[CH3:23]

参加物

6

反応物 4

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 929714-HydroxystilbeneHCID 613145Acetic acid 10-acetoxymethyl-anthracen-9-ylmethyl ester

生成物 1

HCID 41264694-Acetoxy stilbene

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
60 °C

実験手順

To a 4-neck 1 L flask fitted with nechanical agitation, condenser, addition funnel, nitrogen bubbler, and temperature controller was added, in order, THF (450 g), triethylamine (I2.2 g, 0.12 mol), and 4-hydroxy stilbene (19.6 g, 0.10 mol). To this solution at room temperature was slowed added with stirring, via addition funnel, acetic anhdyride (12.3 g, 0.12 mol). When the addition of acetic anhydride was complete, the reaction solution was heated to 60° C. and held at this temperature with stirring for 2 hours. The reaction was cooled to room temperature then THF was removed in vacuo. The resulting residue was diluted with methylene chloride (500 mL) then extracted with 0.1 N HCl (1 ×500 mL), 30% saturated NaHCO3 (1 ×500 mL) and saturated NaCl (1 ×500 mL). The organic layer was dried over anhydrous sodium sulfate then filtered and concentrated in vacuo to give the 4-acetoxy stilbene as a light tan needle-like crystalline powder (22.7 g, 95%).

後処理

  1. customTo a 4-neck 1 L flask fitted with nechanical agitation, condenser, addition funnel, nitrogen bubbler, and temperature controller
  2. additionTo this solution at room temperature was slowed added
  3. stirringwith stirring for 2 hours
  4. temperatureThe reaction was cooled to room temperature
  5. customTHF was removed in vacuo
  6. additionThe resulting residue was diluted with methylene chloride (500 mL)
  7. extractionthen extracted with 0.1 N HCl (1 ×500 mL), 30% saturated NaHCO3 (1 ×500 mL) and saturated NaCl (1 ×500 mL)
  8. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  9. filtrationthen filtered
  10. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-0b36e43fe21747cda47b8b77d89123f3
出典データセット
uspto-grants-1991_03
特許番号
US05001004

反応ノート

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