Aspirin → 2-Acetoxybenzoyl chloride

HRID 2280526Notes

Reaction equation

HRID 2280526 reaction equation
[C:1]([O:4][C:5]1[CH:13]=[CH:12][CH:11]=[CH:10][C:6]=1[C:7](O)=[O:8])(=[O:3])[CH3:2].C(Cl)(C([Cl:18])=O)=O>C1COCC1>[C:1]([O:4][C:5]1[CH:13]=[CH:12][CH:11]=[CH:10][C:6]=1[C:7]([Cl:18])=[O:8])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 2244AspirinHCID 65578Oxalyl chloride

Product 1

HCID 796682-Acetoxybenzoyl chloride

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of compound 2-acetoxybenzoic acid (1.0 g, 5.5 mmol) in THF (30 mL) was added (COCl)2 (0.8 ml, 9.1 mmol) at 0° C. The mixture was heated (reflux, 1.5 h) and concentrated under reduced pressure to afford 2-(chlorocarbonyl)phenyl acetate.

Workup

  1. temperatureThe mixture was heated
  2. temperature(reflux, 1.5 h)
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e65f266fb38949858b0f211c3d850dcf
Source dataset
uspto-grants-2015_09
Patent number
US09139516B2

Reaction notes

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