Hydrochloric Acid → 2-{4-[(3,7-Dimethyl-2,6-octadienyl)oxy]phenyl}acetic acid

HRID 1393849Notes

Reaction equation

HRID 1393849 reaction equation
[OH-].[K+].[CH3:3][C:4]([CH2:19][CH2:20][CH:21]=[C:22]([CH3:24])[CH3:23])=[CH:5][CH2:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][C:15]([O:17]C)=[O:16])=[CH:10][CH:9]=1.Cl>CO>[CH3:3][C:4]([CH2:19][CH2:20][CH:21]=[C:22]([CH3:24])[CH3:23])=[CH:5][CH2:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][C:15]([OH:17])=[O:16])=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 69306599Methyl 2-{4-[(3,7-dimethyl-2,6-octadienyl)oxy]phenyl}acetate

Product 1

HCID 545318442-{4-[(3,7-Dimethyl-2,6-octadienyl)oxy]phenyl}acetic acidYield 61%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1N potassium hydroxide (46 ml) was added to a solution of methyl 2-{4-[(3,7-dimethy-2,6-octadienyl)oxy]phenyl}acetate (9.46 g, 31.28 mmol) in methanol (70 ml) and refluxed for 1 hour. The mixture, with 3N hydrochloric acid (50 ml) added thereto, was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over MgSO4, and then concentrated. The residue was purified by recrystallization (ethyl acetate/hexane), to give 2-{4-[(3,7-dimethyl-2,6-octadienyl)oxy]phenyl}acetic acid (5.50 g, 61%).

Workup

  1. temperaturerefluxed for 1 hour
  2. extractionwas extracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe residue was purified by recrystallization (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-12646011c54340569cd697ee92dfad55
Source dataset
uspto-grants-2008_03
Patent number
US07348017B2

Reaction notes

Loading…