Acetic Anhydride → HCID 4126469, compound

HRID 359338Notes

Reaction equation

HRID 359338 reaction equation
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]

Participants

6

Reactant 4

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

Product 1

HCID 4126469HCID 4126469, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-0b36e43fe21747cda47b8b77d89123f3
Source dataset
uspto-grants-1991_03
Patent number
US05001004

Reaction notes

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