Hydrochloric Acid → 3-acetamidophenoxyacetic acid

HRID 1777124Notes

Reaction equation

HRID 1777124 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([NH:8][C:9](=[O:11])[CH3:10])[CH:5]=[CH:6][CH:7]=1.Br[CH2:13][C:14]([O:16]CC)=[O:15].C([O-])([O-])=O.[K+].[K+].[OH-].[Na+].Cl>CC#N.O.CCO>[C:9]([NH:8][C:4]1[CH:3]=[C:2]([CH:7]=[CH:6][CH:5]=1)[O:1][CH2:13][C:14]([OH:16])=[O:15])(=[O:11])[CH3:10]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 121243-HydroxyacetanilideHCID 14798Sodium Hydroxide

Product 1

HCID 2361233-acetamidophenoxyacetic acid

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 19096565Water ethanolSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred mixture of N-(3-hydroxyphenyl)acetamide (300 mg, 2.0 mmol) in MeCN (5 mL) was added ethyl bromoacetate (500 mg, 3 mmol) and K2CO3 (828 mg, 6 mmol). The mixture was stirred at 80° C. for 4 hours, filtered and the filtrate was concentrated. NaOH (80 mg, 2 mmol) and water:EtOH (1:1, 10 mL) was added to the mixture. This mixture was then stirred at 50° C. for 4 hours before being acidified by 1M HCl, extracted with ethyl acetate (2×30 mL). The combined extracts were washed with brine (30 mL), dried over anhydrous Na2SO4 and concentrated with the residue used directly for the next step. LCMS (m/z): 183.0 (M+1).

Workup

  1. filtrationfiltered
  2. concentrationthe filtrate was concentrated
  3. stirringThis mixture was then stirred at 50° C. for 4 hours
  4. extractionextracted with ethyl acetate (2×30 mL)
  5. washThe combined extracts were washed with brine (30 mL)
  6. dry with materialdried over anhydrous Na2SO4
  7. concentrationconcentrated with the residue

Sources & evidence

ORD record
ord-66601156c8514b648b6ed7d3382f61f7
Source dataset
uspto-grants-2016_02
Patent number
US09266836B2

Reaction notes

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