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 658912Notes

Reaction equation

HRID 658912 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 1N 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 1N NaOH solution, water
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-56b2faf0e602486f89047bdc4a1ad258
Source dataset
uspto-grants-2011_12
Patent number
US08076482B2

Reaction notes

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