Methylparaben → Methyl 4-((2,2-dimethoxy)ethoxy)benzoate

HRID 1072826Notes

Reaction equation

HRID 1072826 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1.[CH3:12][O:13][CH:14]([O:17][CH3:18])[CH2:15]Br.[H-].[Na+]>CN(C)C=O>[CH3:12][O:13][CH:14]([O:17][CH3:18])[CH2:15][O:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 7456MethylparabenHCID 24758Sodium hydrideHCID 816722-Bromo-1,1-dimethoxyethane

Product 1

HCID 22388309Methyl 4-((2,2-dimethoxy)ethoxy)benzoateYield 66.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methyl 4-hydroxybenzoate (15.52 g), bromoacetaldehyde dimethyl acetal (16.90 g) and 60% sodium hydride (5.00 g) were heated in dimethyl formamide (50 ml) at 80° C. for 18 hr. Dimethyl formamide was distilled away from the reaction mixture, and toluene and water were added. The separated toluene layer was dried over magnesium sulfate, and the solvent was distilled away to give the objective compound (16.00 g).

Workup

  1. distillationDimethyl formamide was distilled away from the reaction mixture, and toluene and water
  2. additionwere added
  3. dry with materialThe separated toluene layer was dried over magnesium sulfate
  4. distillationthe solvent was distilled away

Sources & evidence

ORD record
ord-4ffbe891b77040ccacbf0fa0cc4db147
Source dataset
uspto-grants-2005_06
Patent number
US06911469B2

Reaction notes

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