Water → Methyl 4-(2-methoxyethoxymethoxy)benzoate

HRID 517502Notes

Reaction equation

HRID 517502 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][CH:5]=1.[CH3:14][O:15][CH2:16][CH2:17][O:18][CH2:19]Cl.O>O1CCCC1.CN(C)C=O>[CH3:14][O:15][CH2:16][CH2:17][O:18][CH2:19][O:3][C:4]1[CH:5]=[CH:6][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:12][CH:13]=1

Participants

7

Reactant 4

HCID 962WaterHCID 7456MethylparabenHCID 24758Sodium hydrideHCID 775901-(Chloromethoxy)-2-methoxyethane

Product 1

HCID 67056306Methyl 4-(2-methoxyethoxymethoxy)benzoateYield 101.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

3.2 g (78.9 mmol) of 60% sodium hydride are added to a solution of 10 g (65.7 mmol) of methyl 4-hydroxybenzoate in 50 ml of tetrahydrofuran and 50 ml of dimethylformamide. The reaction medium is stirred at ambient temperature for 20 minutes then 8.3 g (72.3 mmol) of 2-methoxyethoxymethyl chloride are added. After stirring for 24 h at ambient temperature, the mixture is poured over water then extracted with ethyl acetate. The organic phase is washed with water then with a saturated aqueous solution of sodium chloride, dried over magnesium sulphate, filtered and concentrated. 16 g (100%) of methyl 4-(2-methoxyethoxymethoxy)benzoate are obtained in the form of a colourless oil.

Workup

  1. stirringAfter stirring for 24 h at ambient temperature
  2. extractionthen extracted with ethyl acetate
  3. washThe organic phase is washed with water
  4. dry with materialwith a saturated aqueous solution of sodium chloride, dried over magnesium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-1d833b80956a492f88193c88ef0f286a
Source dataset
uspto-grants-2015_08
Patent number
US09115102B2

Reaction notes

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