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

HRID 646803Notes

Reaction equation

HRID 646803 reaction equation
C(C1C=CC(C(C)(CCCCC(=O)CCCCC(C2C=CC(CC(C)C)=CC=2)(C)C(O)=O)C(O)=O)=CC=1)C(C)C.C([O:43][C:44](=[O:74])[C:45]([CH3:73])([C:67]1[CH:72]=[CH:71][CH:70]=[CH:69][CH:68]=1)[CH2:46][CH2:47][CH2:48][C:49](=[O:66])[CH2:50][CH2:51][CH2:52][C:53]([CH3:65])([C:59]1[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=1)[C:54]([O:56]CC)=[O:55])C.[OH-].[K+]>O.C(O)C>[CH3:65][C:53]([C:59]1[CH:60]=[CH:61][CH:62]=[CH:63][CH:64]=1)([CH2:52][CH2:51][CH2:50][C:49](=[O:66])[CH2:48][CH2:47][CH2:46][C:45]([CH3:73])([C:67]1[CH:68]=[CH:69][CH:70]=[CH:71][CH:72]=1)[C:44]([OH:74])=[O:43])[C:54]([OH:56])=[O:55]

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 103252762,12-Bis-(4-isobutylphenyl)-2,12-dimethyl-7-oxotridecanedioic acidHCID 11476854Diethyl 2,10-dimethyl-6-oxo-2,10-diphenylundecanedioate

Product 1

HCID 102016332,10-dimethyl-6-oxo-2,10-diphenyl-undecanedioic AcidYield 31.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

According to the procedure given for 210f, 209b (14.5 g, 31.1 mmol) was saponified with KOH (85%, 7.2 g, 108.6 mmol) in water (15 mL) and ethanol (45 mL) at reflux for 6 h. After the usual extractive workup, the crude material was purified by flash chromatography (silica gel; ethyl acetate/hexanes=1/20, 1/10, 1/2) to give 210b (4.0 g, 31%) as a white solid. Mp 44-46° C. 1H NMR (CDCl3): 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 (CDCl3): δ 210.64, 182.66, 142.69, 128.66, 127.18, 126.29, 50.07, 42.97, 38.62, 22.20, 19.11. HRMS (LSIMS, gly): Calcd for C25H31O5 (MH+): 411.2171, found: 411.2144. HPLC: 95.2% pure.

Workup

  1. temperatureat reflux for 6 h
  2. customAfter the usual extractive workup, the crude material was purified by flash chromatography (silica gel; ethyl acetate/hexanes=1/20, 1/10, 1/2)

Sources & evidence

ORD record
ord-7023a3a80bb244ca80052b4d27fbe916
Source dataset
uspto-grants-2010_04
Patent number
US07705177B2

Reaction notes

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