Lithium hydroxide, monohydrate → 4-Oxo-1-phenylcyclohexane-1-carboxylic acid

HRID 852674

反応式

HRID 852674 の反応式
O.[OH-].[Li+].[O:4]=[C:5]1[CH2:10][CH2:9][C:8]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)([C:11]([O:13]C)=[O:12])[CH2:7][CH:6]1C(OC)=O>CO.O.O1CCCC1>[O:4]=[C:5]1[CH2:10][CH2:9][C:8]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)([C:11]([OH:13])=[O:12])[CH2:7][CH2:6]1

参加物

6

反応物 2

HCID 168937Lithium hydroxide, monohydrateHCID 21955247Dimethyl 4-oxo-1-phenyl-1,3-cyclohexanedicarboxylate

生成物 1

HCID 3438864-Oxo-1-phenylcyclohexane-1-carboxylic acid収率 99%

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

Lithium hydroxide monohydrate (11.08 g, 264 mmol) was added to a suspension of dimethyl 4-oxo-1-phenyl-1,3-cyclohexanedicarboxylate (Description 1, 25.5 g, 87.9 mmol) in methanol (250 mL), water (83 mL) and tetrahydrofuran (83 mL) and the mixture was heated under reflux for 3 days. The mixture was cooled and the tetrahydrofuran and methanol were evaporated under reduced pressure. The pH was adjusted to 1 with hydrochloric acid (5M) and the mixture was extracted with dichloromethane. The combined organic fractions were dried (MgSO4) and the solvent was evaporated under reduced pressure to give the title compound as a light yellow solid (19 g, 99%). 1H NMR (400 MHz, CDCl3) δ 7.50-7.29 (5H, m), 2.29-2.73 (2H, m), 2.62-2.55 (2H, m), 2.47-2.41 (2H, m), and 2.35-2.27 (2H, m).

後処理

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 3 days
  3. temperatureThe mixture was cooled
  4. customthe tetrahydrofuran and methanol were evaporated under reduced pressure
  5. extractionthe mixture was extracted with dichloromethane
  6. dry with materialThe combined organic fractions were dried (MgSO4)
  7. customthe solvent was evaporated under reduced pressure

出典と根拠

ORDレコード
ord-dc1d96e7f22246219ffc714aaaca346c
出典データセット
uspto-grants-2007_08
特許番号
US07253205B2

関連ノート

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