Acetic Anhydride → 2-Acetoxy-4-(2.2,3,3,3-pentafluoropropoxy)benzoic acid
Reaction equation
[OH:1][C:2]1[CH:10]=[C:9]([O:11][CH2:12][C:13]([F:19])([F:18])[C:14]([F:17])([F:16])[F:15])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH3:20][C:21](OC(C)=O)=[O:22]>N1C=CC=CC=1>[C:21]([O:1][C:2]1[CH:10]=[C:9]([O:11][CH2:12][C:13]([F:18])([F:19])[C:14]([F:15])([F:16])[F:17])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5])(=[O:22])[CH3:20]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A solution of 2-hydroxy-4-(2,2,3,3,3-pentafluoropropoxy)benzoic acid (obtained in example 6) (0.45 g, 1.6 mmol) in pyridine (3 mL) was cooled to 0° C. and Ac2O (0.25 mL) was added. The resulting mixture was stirred for 15 min at 0° C. and for 2 h at room temperature. The mixture was then concentrated and the residue was treated with H2O (10 mL) and stirred until precipitation (2 h). The solid was collected by filtration and was purified by chromatography on silica-gel using hexane-EtOAc mixtures of increasing polarity as eluent, to afford 0.2 g of the desired product as a white solid (38% yield).
Workup
- concentrationThe mixture was then concentrated
- additionthe residue was treated with H2O (10 mL)
- stirringstirred until precipitation (2 h)
- filtrationThe solid was collected by filtration
- customwas purified by chromatography on silica-gel
- temperatureof increasing polarity as eluent
Sources & evidence
- ORD record
- ord-162ab3b3dde94b2e9cc205d8a97dbf86
- Source dataset
- uspto-grants-2009_09
- Patent number
- US07589125B2
Reaction notes
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