Ethylene Glycol → 3-(4-[1,3]Dioxolan-2-yl-3,5-dimethylphenyl)-propionic acid methyl ester

HRID 1515039Notes

Reaction equation

HRID 1515039 reaction equation
[CH3:1][O:2][C:3](=[O:16])[CH2:4][CH2:5][C:6]1[CH:11]=[C:10]([CH3:12])[C:9]([CH:13]=[O:14])=[C:8]([CH3:15])[CH:7]=1.[CH2:17](O)[CH2:18][OH:19].CC1C=CC(S(O)(=O)=O)=CC=1.O>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3](=[O:16])[CH2:4][CH2:5][C:6]1[CH:11]=[C:10]([CH3:12])[C:9]([CH:13]2[O:19][CH2:18][CH2:17][O:14]2)=[C:8]([CH3:15])[CH:7]=1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 521998p-Toluenesulfonic acid monohydrateHCID 54209618Methyl 3-(3,5-dimethyl-4-formylphenyl)propionate

Product 1

HCID 669660773-(4-[1,3]Dioxolan-2-yl-3,5-dimethylphenyl)-propionic acid methyl ester

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a stirred solution of 3-(4-formyl-3,5-dimethylphenyl)-propionic acid methyl ester, (2.2 g, 10 mmol) and ethane-1,2-diol (1.86 g, 30 mmol) in toluene (50 mL) was added p-TsOH.H2O (38 mg, 0.2 mmol) and the solution was refluxed using a Dean-Stark apparatus overnight. The solvent was removed under reduced pressure and the residue was purified by flash chromatography using heptane/EtOAc (5:1) as eluent to give 3-(4-[1,3]dioxolan-2-yl-3,5-dimethylphenyl)-propionic acid methyl ester as a colorless oil.

Workup

  1. temperaturethe solution was refluxed
  2. customa Dean-Stark apparatus overnight
  3. customThe solvent was removed under reduced pressure
  4. customthe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-6ec3435795b14d4eb106d5368b7bc0c8
Source dataset
uspto-grants-2012_07
Patent number
US08222248B2

Reaction notes

Loading…