2-(4-Chloro-2-[1,3]dioxolan-2-yl-phenoxy)-2-ethyl-butyric acid methyl ester → 2-(4-Chloro-2-formyl-phenoxy)-2-ethyl-butyric acid methyl ester

HRID 504556Notes

Reaction equation

HRID 504556 reaction equation
[CH3:1][O:2][C:3](=[O:22])[C:4]([O:9][C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:11]=1[CH:17]1OCC[O:18]1)([CH2:7][CH3:8])[CH2:5][CH3:6]>FC(F)(F)C(O)=O>[CH3:1][O:2][C:3](=[O:22])[C:4]([O:9][C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:11]=1[CH:17]=[O:18])([CH2:5][CH3:6])[CH2:7][CH3:8]

Participants

3

Reactant 1

HCID 594280672-(4-Chloro-2-[1,3]dioxolan-2-yl-phenoxy)-2-ethyl-butyric acid methyl ester

Product 1

HCID 594280992-(4-Chloro-2-formyl-phenoxy)-2-ethyl-butyric acid methyl esterYield 93.6%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 2-(4-chloro-2-[1,3]dioxolan-2-yl-phenoxy)-2-ethyl-butyric acid methyl ester (16 g, 48.8 mmol) in trifluoroacetic acid (20 mL) was stirred at room temperature for 3 h. Then the mixture was concentrated and the residue was partitioned between EtOAc and water. The organic layer was washed with IN NaOH solution, water, dried over anhydrous Na2SO4 and concentrated to give the title compound (13 g).

Workup

  1. concentrationThen the mixture was concentrated
  2. customthe residue was partitioned between EtOAc and water
  3. washThe organic layer was washed with IN NaOH solution, water
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-03880658acfb40369a879c371a9385be
Source dataset
uspto-grants-2010_08
Patent number
US07776875B2

Reaction notes

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