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

HRID 969016Notes

Reaction equation

HRID 969016 reaction equation
C([O:3][C:4](=[O:34])[C:5]([CH3:33])([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[CH2:6][CH2:7][CH2:8][C:9](=[O:26])[CH2:10][CH2:11][CH2:12][C:13]([CH3:25])([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:14]([O:16]CC)=[O:15])C.[OH-].[K+]>O.C(O)C>[CH3:25][C:13]([C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)([CH2:12][CH2:11][CH2:10][C:9](=[O:26])[CH2:8][CH2:7][CH2:6][C:5]([CH3:33])([C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)[C:4]([OH:34])=[O:3])[C:14]([OH:16])=[O:15]

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 31.3%

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-4a9496d66e4e4da189e5ebd4e600c85c
Source dataset
uspto-grants-2007_12
Patent number
US07304093B2

Reaction notes

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