Citric Acid → (E)-3-(4-(methoxymethoxy)-3,5-dimethylstyryl)benzoic acid

HRID 2368867Notes

Reaction equation

HRID 2368867 reaction equation
[CH3:1][O:2][CH2:3][O:4][C:5]1[C:23]([CH3:24])=[CH:22][C:8](/[CH:9]=[CH:10]/[C:11]2[CH:12]=[C:13]([CH:19]=[CH:20][CH:21]=2)[C:14]([O:16]CC)=[O:15])=[CH:7][C:6]=1[CH3:25].[OH-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1COCC1.CCO.CCOC(C)=O>[CH3:1][O:2][CH2:3][O:4][C:5]1[C:6]([CH3:25])=[CH:7][C:8](/[CH:9]=[CH:10]/[C:11]2[CH:12]=[C:13]([CH:19]=[CH:20][CH:21]=2)[C:14]([OH:16])=[O:15])=[CH:22][C:23]=1[CH3:24]

Participants

7

Reactant 3

HCID 311Citric AcidHCID 14798Sodium HydroxideHCID 68335156(E)-ethyl 3-[4-(methoxymethoxy)-3,5-dimethylstyryl]benzoate

Product 1

HCID 67262065(E)-3-(4-(methoxymethoxy)-3,5-dimethylstyryl)benzoic acidYield 97%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (E)-ethyl 3-[4-(methoxymethoxy)-3,5-dimethylstyryl]benzoate (0.6 g, 1.762 mmol) in THF and EtOH ( 6/2 mL) was added 2N NaOH (1.762 mL, 3.524 mmol) at room temperature. The reaction mixture was stirred overnight (about 18 hours) at room temperature and diluted with EtOAc and acidified with 5% citric acid. The solution was washed with saturated brine and dried with Na2SO4. The solution was filtered and concentrated. (E)-3-[4-(methoxymethoxy)-3,5-dimethylstyryl]benzoic acid (0.533 g, 97%) was obtained without further purification (TLC indicated a pure compound).

Workup

  1. washThe solution was washed with saturated brine
  2. dry with materialdried with Na2SO4
  3. filtrationThe solution was filtered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-aae5823f8882487093c3fe90bf14d677
Source dataset
uspto-grants-2014_04
Patent number
US08703815B2

Reaction notes

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