Potassium Hydroxide → HCID 10203522, compound

HRID 48003Notes

Reaction equation

HRID 48003 reaction equation
C([O:3][C:4](=[O:36])[C:5]([CH3:35])([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[CH2:6][CH2:7][CH2:8][CH2:9][C:10](=[O:28])[CH2:11][CH2:12][CH2:13][CH2:14][C:15]([CH3:27])([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:16]([O:18]CC)=[O:17])C.[OH-].[K+]>C(O)C.O>[O:28]=[C:10]([CH2:11][CH2:12][CH2:13][CH2:14][C:15]([CH3:27])([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[C:16]([OH:18])=[O:17])[CH2:9][CH2:8][CH2:7][CH2:6][C:5]([CH3:35])([C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)[C:4]([OH:36])=[O:3]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 11329409Diethyl 2,12-dimethyl-7-oxo-2,12-diphenyltridecanedioate

Product 1

HCID 10203522HCID 10203522, compoundYield 90.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 7-oxo-2,12-dimethyl-2,12-diphenyl-tridecanedioic acid diethyl ester (3.93 g, 7.55 mmol) in ethanol (60 mL) was added a solution of KOH (4.0 g, 85%, mmol) in water (10 mL). The reaction mixture was heated under reflux for 3 h and then kept overnight at rt. The solution was concentrated under reduced pressure. The residue was dissolved in water (100 mL) and washed with ether (2×75 mL). The aqueous layer was acidified with concd. HCl (ca. 12 mL) until pH 1. The product was extracted with diethyl ether (3×75 mL). The combined organic extracts were dried over MgSO4, filtered, and concentrated in vacuo to give 7-oxo-2,12-dimethyl-2,12-diphenyl-tridecanedioic acid as an oil (3.0 g, 90%). 1H NMR (300 MHz, CDCl3/TMS): δ (ppm): 7.40-7.10 (m, 10H), 2.32 (t, J=7.2 Hz, 4H), 2.10-1.80 (m, 4H), 1.6-1.45 (m, 10H), 1.25-1.10 (m, 4H). 13C NMR (75 MHz, CDCl3/TMS): δ (ppm): 211.1, 182.5, 142.8, 128.4, 126.9, 126.0, 49.9, 42.3, 38.7, 24.2, 24.0, 22.3. HRMS (LSIMS, nba): Calcd. for C27H35O5 (MH+): 439.2484, found 439.2497.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 3 h
  3. concentrationThe solution was concentrated under reduced pressure
  4. dissolutionThe residue was dissolved in water (100 mL)
  5. washwashed with ether (2×75 mL)
  6. extractionThe product was extracted with diethyl ether (3×75 mL)
  7. dry with materialThe combined organic extracts were dried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-576edfa4bb394ed888c4c45d624deb10
Source dataset
uspto-grants-2004_03
Patent number
US06699910B2

Reaction notes

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