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 1515040Notes

Reaction equation

HRID 1515040 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-a69c2b4806954a95a2af56f559f987de
Source dataset
uspto-grants-2012_07
Patent number
US08222248B2

Reaction notes

Loading…