Potassium Hydroxide → HCID 11738543, compound

HRID 239058Notes

Reaction equation

HRID 239058 reaction equation
C(C1C=C[C:8]([C:11]([CH3:40])([CH2:15][CH2:16][CH2:17][CH2:18][C:19](=[O:39])[CH2:20][CH2:21][CH2:22][CH2:23][C:24]([C:29]2C=CC(CC(C)C)=CC=2)([CH3:28])[C:25]([OH:27])=[O:26])[C:12]([OH:14])=[O:13])=CC=1)C(C)C.[OH-].[K+]>C(O)C.O>[O:39]=[C:19]([CH2:20][CH2:21][CH2:22][CH2:23][C:24]([CH3:29])([CH3:28])[C:25]([OH:27])=[O:26])[CH2:18][CH2:17][CH2:16][CH2:15][C:11]([CH3:8])([CH3:40])[C:12]([OH:14])=[O:13]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 103252762,12-Bis-(4-isobutylphenyl)-2,12-dimethyl-7-oxotridecanedioic acid

Product 1

HCID 11738543HCID 11738543, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

According to the procedure given for 210f, 209c (30.0 g, 81.0 mmol) was saponified with KOH (85%, 18.9 g, 286 mmol) in ethanol (143 mL) and water (48 mL) at reflux for 5 h. The solid product obtained after extraction and drying was purified by flash chromatography (silica; hexanes/ethyl acetate=90/10) to afford 210c (22.0 g, 86%) as a white solid. Mp 60-61.5° C. 1H NMR (CDCl3): δ 11.40 (br., 2 H), 2.41 (t, 4H, J=7.3), 1.62-1.48 (m, 8 μl), 1.32-1.18 (m, 4 H), 1.18 (s, 12 H). 13C NMR (CDCl3=77.0 ppm): δ 211.11, 184.74, 42.49, 42.14, 40.42, 24.92, 24.62, 23.99. HRMS (LSIMS, gly): Calcd for C17H31O5 (MH+): 315.2171, found: 315.2183. HPLC: 94.5% pure. Anal. (C17H30O5) C, H.

Workup

  1. temperatureat reflux for 5 h
  2. customThe solid product obtained
  3. extractionafter extraction
  4. customdrying
  5. customwas purified by flash chromatography (silica; hexanes/ethyl acetate=90/10)

Sources & evidence

ORD record
ord-e3734ef332e74942aa08d87a11674a49
Source dataset
uspto-grants-2014_02
Patent number
US08642653B2

Reaction notes

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