3-(4-[1,3]Dioxolan-2-yl-3,5-dimethylphenyl)-2,2-dimethylpropionic acid methyl ester → Methyl 3-(4-formyl-3,5-dimethylphenyl)-2,2-dimethylpropanoate

HRID 1360780Notes

Reaction equation

HRID 1360780 reaction equation
[CH3:1][O:2][C:3](=[O:21])[C:4]([CH3:20])([CH3:19])[CH2:5][C:6]1[CH:11]=[C:10]([CH3:12])[C:9]([CH:13]2OCC[O:14]2)=[C:8]([CH3:18])[CH:7]=1>CC(C)=O.O>[CH3:1][O:2][C:3](=[O:21])[C:4]([CH3:19])([CH3:20])[CH2:5][C:6]1[CH:11]=[C:10]([CH3:12])[C:9]([CH:13]=[O:14])=[C:8]([CH3:18])[CH:7]=1

Participants

4

Reactant 1

HCID 669656633-(4-[1,3]Dioxolan-2-yl-3,5-dimethylphenyl)-2,2-dimethylpropionic acid methyl ester

Product 1

HCID 86632822Methyl 3-(4-formyl-3,5-dimethylphenyl)-2,2-dimethylpropanoate

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

To a stirred solution of 3-(4-[1,3]dioxolan-2-yl-3,5-dimethylphenyl)-2,2-dimethylpropionic acid methyl ester (1.7 g, 5.8 mmol) in acetone (20 mL) and water (0.3 mL) was added Amberlyst-15 (233 mg). The suspension was stirred at ambient temperature overnight and the suspension was filtered and washed with acetone. The solvent was removed under reduced pressure and the residue was purified by flash chromatography using heptane/EtOAc (5:1) to give 3-(4-formyl-3,5-dimethylphenyl)-2,2-dimethylpropionic acid methyl ester as a pale-yellow oil.

Workup

  1. filtrationthe suspension was filtered
  2. washwashed with acetone
  3. customThe solvent was removed under reduced pressure
  4. customthe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-e73ae89832d84fa0bed446b0e16f36e7
Source dataset
uspto-grants-2011_02
Patent number
US07879850B2

Reaction notes

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