Hydrochloric Acid → 1-(4-Methoxyphenyl)cyclohexanecarboxylic acid

HRID 2375204Notes

Reaction equation

HRID 2375204 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2([C:15]#N)[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)=[CH:5][CH:4]=1.[OH-:17].[Na+].Cl.[OH2:20]>O1CCOCC1.OO>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2([C:15]([OH:20])=[O:17])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962Water2×HCID 14798Sodium HydroxideHCID 986291-(4-Methoxyphenyl)cyclohexanecarbonitrile

Product 1

HCID 819791-(4-Methoxyphenyl)cyclohexanecarboxylic acidYield 71%

Reagents, catalysts & solvents 2

HCID 784Hydrogen PeroxideSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 1-(4-methoxyphenyl)cyclohexanecarbonitrile (E2) (1.092 g, 5.07 mmol) in dioxane (6 ml) to a mixture of 2 M NaOH in water (150 ml) and 30% H2O2 in water (7.5 ml) was added and the resultant suspension was stirred under reflux for 4 days. The pH of the reaction medium was brought to pH 1 with conc. HCl (ca. 30 ml) and the obtained mixture was extracted with ethyl acetate (4×80 ml). The combined organic extract was washed with brine (50 ml) and dried (Na2SO4). The solvent was evaporated and the residue was chromatographed on silicagel (50 g) with benzene-ethyl acetate-acetic acid (9:1:0.15) as eluent affording the title compound (0.844 g, 71%) as a white solid. 1H NMR (CDCl3, HMDSO) δ: 1.05-1.91 (8H, m); 2.16-2.61 (2H, m); 3.76 (3H, s); 6.86 (2H, d, J=9.0 Hz); 7.34 (2H, d, J=9.0 Hz); 11.26 (1H, br s).

Workup

  1. additionwas added
  2. temperatureunder reflux for 4 days
  3. extractionthe obtained mixture was extracted with ethyl acetate (4×80 ml)
  4. extractionThe combined organic extract
  5. washwas washed with brine (50 ml)
  6. dry with materialdried (Na2SO4)
  7. customThe solvent was evaporated
  8. customthe residue was chromatographed on silicagel (50 g) with benzene-ethyl acetate-acetic acid (9:1:0.15) as eluent

Sources & evidence

ORD record
ord-2cb3713cad95455283cfcfb11753ea53
Source dataset
uspto-grants-2008_12
Patent number
US07465719B2

Reaction notes

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