Potassium Hydroxide → Acetic acid, 5-methoxy-m-tolyl-

HRID 1760015Notes

Reaction equation

HRID 1760015 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:10][C:11]#N)[CH:6]=[C:7]([CH3:9])[CH:8]=1.[OH-:13].[K+].[OH2:15].CC(O)C>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:10][C:11]([OH:15])=[O:13])[CH:6]=[C:7]([CH3:9])[CH:8]=1

Participants

4

Reactant 3

HCID 14797Potassium HydroxideHCID 21889133Propan-2-ol--water (1/1)HCID 22048241(3-Methoxy-5-methylphenyl)acetonitrile

Product 1

HCID 39879Acetic acid, 5-methoxy-m-tolyl-Yield 80%

Conditions

Temperature
120 °C

Procedure

A solution of 3-methoxy-5-methylphenylacetonitrile (9 g; 0.06 mol; 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 reaction mixture was concentrated and extracted with ether. The aqueous phase was acidified and extracted twice with ether. The combined organic layers were washed with water, dried (Na2SO4), and evaporated to a residue which was dissolved in EtOH, treated with activated carbon, filtered, and evaporated to yield the sub-title compound (8.1 g; 80%) as yellow crystals.

Workup

  1. waitat room temperature for 2 days
  2. concentrationThe reaction mixture was concentrated
  3. extractionextracted with ether
  4. extractionextracted twice with ether
  5. washThe combined organic layers were washed with water
  6. dry with materialdried (Na2SO4)
  7. customevaporated to a residue which
  8. dissolutionwas dissolved in EtOH
  9. additiontreated with activated carbon
  10. filtrationfiltered
  11. customevaporated

Sources & evidence

ORD record
ord-13218de8eb28454cbb91662d2fd9c665
Source dataset
uspto-grants-2005_01
Patent number
US06838478B2

Reaction notes

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