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

HRID 618768Notes

Reaction equation

HRID 618768 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].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

4

Reactant 2

HCID 313Hydrochloric AcidHCID 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 sodim 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 cooling sodim borohydride (0.25 g)
  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-b2d8fba2da4442f6998a58e171798ffa
Source dataset
uspto-grants-1999_09
Patent number
US05955505

Reaction notes

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