Potassium Hydroxide → 2,10-dimethyl-6-oxo-2,10-diphenyl-undecanedioic Acid

HRID 47990Notes

Reaction equation

HRID 47990 reaction equation
[OH-].[K+].C([O:5][C:6](=[O:36])[C:7]([CH3:35])([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[CH2:8][CH2:9][CH2:10][C:11](=[O:28])[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>O.C(O)C>[CH3:27][C:15]([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)([CH2:14][CH2:13][CH2:12][C:11](=[O:28])[CH2:10][CH2:9][CH2:8][C:7]([CH3:35])([C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)[C:6]([OH:36])=[O:5])[C:16]([OH:18])=[O:17]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 11476854Diethyl 2,10-dimethyl-6-oxo-2,10-diphenylundecanedioate

Product 1

HCID 102016332,10-dimethyl-6-oxo-2,10-diphenyl-undecanedioic AcidYield 31.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a homogenous solution of KOH (85%, 7.17 g, 108.90 mmol) in water (15 mL) and ethanol (45 mL) was added 2,10-dimethyl-6-oxo-2,10-diphenyl-undecanedioic acid diethyl ester (14.5 g, 31.12 mmol). The reaction solution was heated to reflux for 6 h. The ethanol was removed in reduced pressure and the residue was diluted with water (300 mL). The solution was acidified with concd. HCl (18 mL) to pH 1 and extracted with CH2Cl2 (3×100 mL). The combined organic layers were washed with brine, dried over anhydrous Na2SO4 and purified by flash chromatography (silica gel, ethyl acetate/hexanes=1/20, 1/10, 1/2) to furnish 2,10-dimethyl-6-oxo-2,10-diphenyl-undecanedioic acid (4 g, 31.4%) as a white solid. Mp.: 44-46° C. 1H NMR (300 MHz, CDCl3/TMS): δ (ppm) 10.25 (br, 2H), 7.35-7.22 (m, 10H), 2.32 (m, 4H), 1.94-1.86 (m, 4H), 1.57 (s, 6H), 1.51-1.22 (m, 4H). 13C NMR (75 MHz, CDCl3/TMS): δ (ppm) 210.64, 182.66, 142.69, 128.66, 127.18; 126.29, 50.07, 42.97, 38.62, 22.20, 19.11. HRMS (LSIMS, nba): Calcd. for C25H31O5 (MH+): 411.2171, found: 411.2144.

Workup

  1. temperatureThe reaction solution was heated
  2. temperatureto reflux for 6 h
  3. customThe ethanol was removed in reduced pressure
  4. additionthe residue was diluted with water (300 mL)
  5. extractionHCl (18 mL) to pH 1 and extracted with CH2Cl2 (3×100 mL)
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried over anhydrous Na2SO4
  8. custompurified by flash chromatography (silica gel, ethyl acetate/hexanes=1/20, 1/10, 1/2)

Sources & evidence

ORD record
ord-63ba2539b4b5480381f1321c4b07d4fc
Source dataset
uspto-grants-2004_03
Patent number
US06699910B2

Reaction notes

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