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

HRID 2375204

反応式

HRID 2375204 の反応式
[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

参加物

7

反応物 4

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

生成物 1

HCID 819791-(4-Methoxyphenyl)cyclohexanecarboxylic acid収率 71%

試薬・触媒・溶媒 2

HCID 784Hydrogen Peroxide溶媒HCID 312751,4-Dioxane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-2cb3713cad95455283cfcfb11753ea53
出典データセット
uspto-grants-2008_12
特許番号
US07465719B2

関連ノート

読み込み中…