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

HRID 852674

반응식

HRID 852674 반응식
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

참가 물질

6

반응물 2

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

생성물 1

HCID 3438864-Oxo-1-phenylcyclohexane-1-carboxylic acid수율 99%

시약·촉매·용매 3

HCID 887Methanol용매HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-dc1d96e7f22246219ffc714aaaca346c
출처 데이터셋
uspto-grants-2007_08
특허 번호
US07253205B2

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