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

HRID 966965Notes

Reaction equation

HRID 966965 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-96bb9ff9c90e4fe79362a276a4c4d173
Source dataset
uspto-grants-2005_10
Patent number
US06953792B2

Reaction notes

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