Ethanol → 2-(5-Chloro-2-methoxyphenyl)acetic acid

HRID 11650Notes

Reaction equation

HRID 11650 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:11][CH3:12])=[C:6](CC#N)[CH:7]=1.[OH-:13].[K+].[CH2:15]([OH:17])[CH3:16]>O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:11][CH3:12])=[C:6]([CH2:16][C:15]([OH:13])=[O:17])[CH:7]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 14797Potassium HydroxideHCID 7131175(5-Chloro-2-methoxyphenyl)acetonitrile

Product 1

HCID 15040472-(5-Chloro-2-methoxyphenyl)acetic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of (5-chloro-2-methoxy-phenyl)-acetonitrile (17.2 g, 96.3 mmol) in ethanol (200 mL) and water (20 mL) was added potassium hydroxide (27 g, 481 mmol). The reaction was heated to reflux for 12 hours, cooled and the ethanol was removed by concentrating in vacuo. The remaining solution was acidified with aqueous hydrochloric acid (3 M) and extracted with diethyl ether. The organic layer was dried over magnesium sulfate and concentrated in vacuo to give the title compound (15.6 g).

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 12 hours
  3. temperaturecooled
  4. customthe ethanol was removed
  5. concentrationby concentrating in vacuo
  6. extractionextracted with diethyl ether
  7. dry with materialThe organic layer was dried over magnesium sulfate
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-92658eed56284b4f93b9c8db08f2391b
Source dataset
uspto-grants-2006_08
Patent number
US07098212B2

Reaction notes

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