Hydrochloric Acid → N-(ethoxycarbonylmethyl)-2-(4-hydroxymethylphenoxy)acetamide

HRID 2082577Notes

Reaction equation

HRID 2082577 reaction equation
[CH2:1]([O:3][C:4]([CH2:6][NH:7][C:8](=[O:19])[CH2:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([CH:17]=[O:18])=[CH:13][CH:12]=1)=[O:5])[CH3:2].[BH4-].[Na+].Cl>C(O)C>[CH2:1]([O:3][C:4]([CH2:6][NH:7][C:8](=[O:19])[CH2:9][O:10][C:11]1[CH:12]=[CH:13][C:14]([CH2:17][OH:18])=[CH:15][CH:16]=1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 21848352N-(ethoxycarbonylmethyl)-2-(4-formylphenoxy)acetamide

Product 1

HCID 21848389N-(ethoxycarbonylmethyl)-2-(4-hydroxymethylphenoxy)acetamideYield 86.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of N-(ethoxycarbonylmethyl)-2-(4-formylphenoxy)acetamide (4.6 g) and ethanol (150 ml) was added under ice cooling sodium borohydride (0.25 g), and the mixture was stirred at room temperature for 30 minutes. To the reaction mixture was added 3% hydrochloric acid, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. Evaporation of the solvent under reduced pressure gave N-(ethoxycarbonylmethyl)-2-(4-hydroxymethylphenoxy)acetamide (4.03 g).

Workup

  1. additionwas added under ice
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with a saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customEvaporation of the solvent under reduced pressure

Sources & evidence

ORD record
ord-1804c0c139214dfba2088e34716bccc5
Source dataset
uspto-grants-1993_02
Patent number
US05189211

Reaction notes

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