Hydrochloric Acid → 2-(3-Methoxyphenoxy)acetic acid

HRID 1777109Notes

Reaction equation

HRID 1777109 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([OH:9])[CH:6]=[CH:7][CH:8]=1.Br[CH2:11][C:12]([O:14]CC)=[O:13].C([O-])([O-])=O.[K+].[K+].[OH-].[Na+].Cl>CC#N.O.CCO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:6]=[CH:7][CH:8]=1)[O:9][CH2:11][C:12]([OH:14])=[O:13]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 7748Ethyl bromoacetateHCID 90073-MethoxyphenolHCID 11430Potassium CarbonateHCID 14798Sodium Hydroxide

Product 1

HCID 749692-(3-Methoxyphenoxy)acetic acid

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 19096565Water ethanolSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred mixture of 3-methoxyphenol (200 mg, 1.61 mmol) in MeCN (5 mL) was added ethyl bromoacetate (402 mg, 2.42 mmol) and K2CO3 (672 mg, 4.83 mmol). The mixture was stirred at 80° C. for 4 hours, filtered and the filtrate concentrated. NaOH (129 mg, 3.22 mmol) and H2O/EtOH (1:1, 10 mL) was added to the mixture. The reaction mixture was stirred at 50° C. for 4 hours then acidified by 1M HCl and then extracted with ethyl acetate (2×30 mL). The combined organic 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 concentrated
  3. stirringThe reaction mixture was stirred at 50° C. for 4 hours
  4. extractionextracted with ethyl acetate (2×30 mL)
  5. washThe combined organic extracts were washed with brine (30 mL)
  6. dry with materialdried over anhydrous Na2SO4
  7. concentrationconcentrated with the residue

Sources & evidence

ORD record
ord-87868751ae3440479bfc0a639b3a9ff3
Source dataset
uspto-grants-2016_02
Patent number
US09266836B2

Reaction notes

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