Potassium Hydroxide → 2,12-Dimethyl-7-oxo-2,12-di-p-tolyltridecanedioic acid

HRID 239060Notes

Reaction equation

HRID 239060 reaction equation
[CH2:1]([C:5]1[CH:10]=[CH:9][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]2[CH:34]=[CH:33][C:32]([CH2:35]C(C)C)=[CH:31][CH:30]=2)([CH3:28])[C:25]([OH:27])=[O:26])[C:12]([OH:14])=[O:13])=[CH:7][CH:6]=1)C(C)C.C(OC(=O)C(C)(C1C=CC(C)=CC=1)CCCCC(=O)CCCCC(C)(C1C=CC(C)=CC=1)C(OCC)=O)C.[OH-].[K+]>O.C(O)C>[CH3:28][C:24]([C:29]1[CH:34]=[CH:33][C:32]([CH3:35])=[CH:31][CH:30]=1)([CH2:23][CH2:22][CH2:21][CH2:20][C:19](=[O:39])[CH2:18][CH2:17][CH2:16][CH2:15][C:11]([CH3:40])([C:8]1[CH:7]=[CH:6][C:5]([CH3:1])=[CH:10][CH:9]=1)[C:12]([OH:14])=[O:13])[C:25]([OH:27])=[O:26]

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 103252762,12-Bis-(4-isobutylphenyl)-2,12-dimethyl-7-oxotridecanedioic acidHCID 114665792,12-Dimethyl-7-oxo-2,12-di-p-tolyl-tridecanedioic acid diethyl ester

Product 1

HCID 103898292,12-Dimethyl-7-oxo-2,12-di-p-tolyltridecanedioic acidYield 39%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

According to the procedure given for 210f, 209e (9.0 g, 17.2 mmol) was hydrolyzed with KOH (85%, 4.0 g, 60.6 mmol) in water (10 mL) and ethanol (30 mL) at reflux for 6 h. After the usual extractive workup, the crude material was purified by flash chromatography (silica gel; ethyl acetate/hexanes=1/10, 1/6, 1/2) to give 210e (3.1 g, 39%) as a white solid. Mp 48-50° C. 1H NMR (CDCl3): δ 10.8-8.8 (br., 2 H), 7.22 (d, 4H, J=8.1), 7.12 (d, 4H, J=8.1), 2.36 (t, 4H, J=7.5), 2.31 (s, 6 H), 1.98-1.80 (m, 4 H), 1.56-1.44 (m, 4 H), 1.51 (s, 6 H), 1.24-1.15 (m, 4 H). 13C NMR (CDCl3): δ 211.63, 183.07, 140.40, 137.00, 129.58, 126.43, 50.02, 42.82, 39.10, 24.74, 24.50, 22.82, 21.39. HRMS (LSIMS, gly): Calcd for C29H39O5 (MH+): 467.2797, found: 467.2785. HPLC: 92.4% pure. Anal. (C29H38O5) C, H.

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=1/10, 1/6, 1/2)

Sources & evidence

ORD record
ord-9e3d7b10e1914b83a79003136963611c
Source dataset
uspto-grants-2014_02
Patent number
US08642653B2

Reaction notes

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