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

HRID 852674Notes

Reaction equation

HRID 852674 reaction equation
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

Participants

6

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-dc1d96e7f22246219ffc714aaaca346c
Source dataset
uspto-grants-2007_08
Patent number
US07253205B2

Reaction notes

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