Sodium Hydroxide → N-[4-(2-hydroxyethyl)phenyl]acetamide

HRID 483371Notes

Reaction equation

HRID 483371 reaction equation
C([O:4][CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14](=[O:16])[CH3:15])=[CH:9][CH:8]=1)(=O)C.[OH-].[Na+]>CO>[OH:4][CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14](=[O:16])[CH3:15])=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 125713974-Acetamidophenethyl acetate

Product 1

HCID 3295905N-[4-(2-hydroxyethyl)phenyl]acetamideYield 115.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of the product from step (b) (55.3 g) in methanol (250 ml) and 1N aqu. NaOH (500 ml) was stirred at room temperature for 1 hour. The methanol was evaporated in vacuo and the remaining aqueous solution adjusted to pH 4 (2N aqu. HCl), saturated with NaCl, and extracted with ethyl acetate (×3). The combined extracts were washed with water and brine, dried over MgSO4 and evaporated in vacuo to give a brown oil which was flash chromatographed through a silica column using ethyl acetate and then crystallised from ethyl acetate to give the desired product (51.7 g).

Workup

  1. customThe methanol was evaporated in vacuo
  2. extractionextracted with ethyl acetate (×3)
  3. washThe combined extracts were washed with water and brine
  4. dry with materialdried over MgSO4
  5. customevaporated in vacuo
  6. customto give a brown oil which
  7. customchromatographed through a silica column
  8. customcrystallised from ethyl acetate

Sources & evidence

ORD record
ord-1272854cfeea4a5086343221f74d5334
Source dataset
uspto-grants-1993_07
Patent number
US05225431

Reaction notes

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