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

HRID 1777097Notes

Reaction equation

HRID 1777097 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[C:5]#[N:6].Br[CH2:11][C:12]([O:14]CC)=[O:13].C([O-])([O-])=O.[K+].[K+].[OH-].[Na+].Cl>CC#N.O.CCO>[C:5]([C:4]1[CH:3]=[C:2]([CH:9]=[CH:8][CH:7]=1)[O:1][CH2:11][C:12]([OH:14])=[O:13])#[N:6]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 133943-CyanophenolHCID 14798Sodium Hydroxide

Product 1

HCID 122222682-(3-cyanophenoxy)acetic acid

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 19096565Water ethanolSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred mixture of 3-hydroxybenzonitrile (100 mg, 0.840 mmol) in MeCN (5 mL) was added ethyl bromoacetate (209 mg, 1.26 mmol) and K2CO3 (350 mg, 2.52 mmol). The mixture was stirred at 80° C. for 4 hours until TLC showed completion of the reaction. The mixture was filtered and the filtrate concentrated. NaOH (67 mg, 1.68 mmol) and water:EtOH (1:1, 10 mL) was added to the residue and the mixture stirred at 50° C. for 4 hours. After cooling, the mixture was 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. The residue was used directly in the next step. LCMS (m/z): 178.0 (M+1).

Workup

  1. customcompletion of the reaction
  2. filtrationThe mixture was filtered
  3. concentrationthe filtrate concentrated
  4. stirringthe mixture stirred at 50° C. for 4 hours
  5. temperatureAfter cooling
  6. extractionextracted with ethyl acetate (2×30 mL)
  7. washThe combined extracts were washed with brine (30 mL)
  8. dry with materialdried over anhydrous Na2SO4
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-c51e6cde54ff4a5fafe78644fa973e99
Source dataset
uspto-grants-2016_02
Patent number
US09266836B2

Reaction notes

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