Acetic Anhydride → Benzoin acetate

HRID 1753716Notes

Reaction equation

HRID 1753716 reaction equation
[C:1]1([C:7]([CH:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[OH:10])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:17](OC(=O)C)(=[O:19])[CH3:18]>S(=O)(=O)(O)O.O>[C:17]([O:8][CH:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[C:9](=[O:10])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)(=[O:19])[CH3:18]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 8400Benzoin

Product 1

HCID 95416Benzoin acetate

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 962WaterSolvent

Procedure

Benzoin 23 (2.0 g, 9.40 mmol) was dissolved in acetic anhydride (15 mL, 158.70 mmol) followed by the addition of two drops of sulfuric acid which resulted in a pale yellow color. The reaction mixture was then stirred under a nitrogen atmosphere at room temperature (72 h) while monitoring its progress by TLC. The reaction mixture was then dissolved in water and extracted with dichloromethane (3×40 mL). The dichloromethane layer was then dried over anhydrous sodium sulfate. After removal of the drying agent by filtration and removal of the solvent by rotary evaporation, the product was found to be of acceptable purity as evidenced by 1H NMR and TLC, Rf: 0.2 (hexane/ethyl acetate, 2:1): mp 83-85° C. (Lit. 85-87° C.).

Workup

  1. customresulted in a pale yellow color
  2. extractionextracted with dichloromethane (3×40 mL)
  3. dry with materialThe dichloromethane layer was then dried over anhydrous sodium sulfate
  4. customAfter removal of the drying agent
  5. filtrationby filtration and removal of the solvent
  6. customby rotary evaporation
  7. custommp 83-85° C. (Lit. 85-87° C.)

Sources & evidence

ORD record
ord-1fccccede2e14235b2222f7fc92134e0
Source dataset
uspto-grants-2015_10
Patent number
US09167820B2

Reaction notes

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