Hydrochloric Acid → 4-(2-Methoxyethoxymethoxy)benzoic acid

HRID 517503Notes

Reaction equation

HRID 517503 reaction equation
[OH-].[Na+].[CH3:3][O:4][CH2:5][CH2:6][O:7][CH2:8][O:9][C:10]1[CH:19]=[CH:18][C:13]([C:14]([O:16]C)=[O:15])=[CH:12][CH:11]=1.Cl>O1CCCC1.O.CO.C(OCC)(=O)C>[CH3:3][O:4][CH2:5][CH2:6][O:7][CH2:8][O:9][C:10]1[CH:19]=[CH:18][C:13]([C:14]([OH:16])=[O:15])=[CH:12][CH:11]=1

Participants

8

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67056306Methyl 4-(2-methoxyethoxymethoxy)benzoate

Product 1

HCID 149522434-(2-Methoxyethoxymethoxy)benzoic acidYield 95%

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
40 °C

Procedure

15 g (375 mmol) of sodium hydroxide powder are added to a solution of 18 g (75 mmol) of methyl 4-(2-methoxyethoxymethoxy)benzoate in 250 ml of tetrahydrofuran, 80 ml of water and 30 ml of methanol. The reaction medium is stirred at 40° C. for 18 h then hydrolysed, diluted with ethyl acetate and brought to pH=6 with an aqueous solution of hydrochloric acid having a concentration of 1N. After extracting with ethyl acetate, the organic phase is washed with water then with a saturated aqueous solution of sodium chloride, dried over magnesium sulphate, filtered then concentrated. 16 g (95%) of 4-(2-methoxyethoxy-methoxy)benzoic acid are obtained in the form of a white solid.

Workup

  1. extractionAfter extracting with ethyl acetate
  2. washthe organic phase is washed with water
  3. dry with materialwith a saturated aqueous solution of sodium chloride, dried over magnesium sulphate
  4. filtrationfiltered
  5. concentrationthen concentrated

Sources & evidence

ORD record
ord-bff7e72dbcd14408a47dbbf1d41647de
Source dataset
uspto-grants-2015_08
Patent number
US09115102B2

Reaction notes

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