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

HRID 2375204

반응식

HRID 2375204 반응식
[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

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 962Water2회HCID 14798Sodium HydroxideHCID 986291-(4-Methoxyphenyl)cyclohexanecarbonitrile

생성물 1

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

시약·촉매·용매 2

HCID 784Hydrogen Peroxide용매HCID 312751,4-Dioxane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-2cb3713cad95455283cfcfb11753ea53
출처 데이터셋
uspto-grants-2008_12
특허 번호
US07465719B2

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