Water → Ethyl 2-(4-acetamidophenoxy)acetate

HRID 1777111Notes

Reaction equation

HRID 1777111 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:11])[CH3:10])=[CH:4][CH:3]=1.Br[C:13](C)(C)[C:14]([O:16][CH2:17][CH3:18])=[O:15].C([O-])([O-])=O.[K+].[K+].O>CC#N>[C:9]([NH:8][C:5]1[CH:4]=[CH:3][C:2]([O:1][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:7][CH:6]=1)(=[O:11])[CH3:10]

Participants

6

Reactant 4

HCID 962WaterHCID 1983AcetaminophenHCID 11430Potassium CarbonateHCID 11745Propanoic acid, 2-bromo-2-methyl-, ethyl ester

Product 1

HCID 309738Ethyl 2-(4-acetamidophenoxy)acetate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of N-(4-hydroxyphenyl)acetamide (500 mg, 3.31 mmol) in CH3CN (10 mL) was added ethyl 2-bromo-2-methylpropanoate (663 mg, 3.97 mmol) and K2CO3 (3 g, 21.7 mmol) at 25° C. The mixture was heated at reflux for 16 h. The mixture had water (100 mL) added and extracted with ethyl acetate (2×50 mL). The combined organic layers were washed with brine (30 mL), dried over Na2SO4 and concentrated to give the title compound which was used in next step without further purification.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 16 h
  3. additionadded
  4. extractionextracted with ethyl acetate (2×50 mL)
  5. washThe combined organic layers were washed with brine (30 mL)
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-9fcf1934e6cf4d42874d8698f01278f6
Source dataset
uspto-grants-2016_02
Patent number
US09266836B2

Reaction notes

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