Hydrochloric Acid → 2-Benzyloxy-5-(2-methoxymethoxyethyl)benzoic acid

HRID 1862619Notes

Reaction equation

HRID 1862619 reaction equation
[CH2:1]([O:8][C:9]1[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][O:21][CH2:22][O:23][CH3:24])=[CH:15][C:10]=1[C:11]([O:13]C)=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].Cl>CO>[CH2:1]([O:8][C:9]1[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][O:21][CH2:22][O:23][CH3:24])=[CH:15][C:10]=1[C:11]([OH:13])=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 18620180HCID 18620180, compound

Product 1

HCID 186201312-Benzyloxy-5-(2-methoxymethoxyethyl)benzoic acidYield 95.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of methyl 2-benzyloxy-5-(2-methoxymethoxyethyl)benzoate (1.34 g) in methanol (15 ml) was added 2N aqueous sodium hydroxide solution (4.0 ml), and the mixture was heated under reflux for 40 minutes with stirring. After the reaction mixture was cooled to 0° C. 2N hydrochloric acid (5.0 ml) was added and the resulting mixture was extracted with dichloromethane. The extract was washed with brine and dried over anhydrous magnesium sulfate. After the solvent was removed under reduced pressure, crystallization of the residue from hexane and diethyl ether (1/1) gave 2-benzyloxy-5-(2methoxymethoxyethyl)benzoic acid (1.23 g).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 40 minutes
  3. extractionthe resulting mixture was extracted with dichloromethane
  4. washThe extract was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customAfter the solvent was removed under reduced pressure, crystallization of the residue from hexane and diethyl ether (1/1)

Sources & evidence

ORD record
ord-03bcaa579d7443b792f32ba803d5b4da
Source dataset
uspto-grants-2003_03
Patent number
US06538152B1

Reaction notes

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