Potassium Hydroxide → 2-(3-Chloro-5-methylphenyl)acetic acid

HRID 1760022Notes

Reaction equation

HRID 1760022 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]#N)[CH:5]=[C:6]([CH3:8])[CH:7]=1.[OH-:12].[K+].[OH2:14].CC(O)C>>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([OH:14])=[O:12])[CH:5]=[C:6]([CH3:8])[CH:7]=1

Participants

4

Reactant 3

HCID 14797Potassium HydroxideHCID 21889133Propan-2-ol--water (1/1)HCID 226001322-(3-Chloro-5-methylphenyl)acetonitrile

Product 1

HCID 226000812-(3-Chloro-5-methylphenyl)acetic acidYield 70%

Conditions

Temperature
120 °C

Procedure

A mixture 3-chloro-5-methylphenylacetonitrile (13.3 g; from step (ii) above) and KOH (17 g; 0.3 mol) in 150 mL of water:i-PrOH (2:1) was heated while stirring in an autoclave at 120° C. overnight and then at room temperature for 2 days. The i-PrOH was evaporated and the remainder was acidified (6M HCl) to pH 2 and extracted 3 times with ether. The combined organic layers were washed twice with water, dried (Na2SO4), and evaporated to yield the sub-title compound (10.4 g; 70%).

Workup

  1. waitat room temperature for 2 days
  2. customThe i-PrOH was evaporated
  3. extractionextracted 3 times with ether
  4. washThe combined organic layers were washed twice with water
  5. dry with materialdried (Na2SO4)
  6. customevaporated

Sources & evidence

ORD record
ord-db595e9683f24b4db28d7c74f262a1a7
Source dataset
uspto-grants-2005_01
Patent number
US06838478B2

Reaction notes

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