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

HRID 969018Notes

Reaction equation

HRID 969018 reaction equation
C([O:3][C:4](=[O:38])[C:5]([CH3:37])([C:30]1[CH:35]=[CH:34][C:33]([CH3:36])=[CH:32][CH:31]=1)[CH2:6][CH2:7][CH2:8][CH2:9][C:10](=[O:29])[CH2:11][CH2:12][CH2:13][CH2:14][C:15]([CH3:28])([C:21]1[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=1)[C:16]([O:18]CC)=[O:17])C.[OH-].[K+]>O.C(O)C>[CH3:28][C:15]([C:21]1[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=1)([CH2:14][CH2:13][CH2:12][CH2:11][C:10](=[O:29])[CH2:9][CH2:8][CH2:7][CH2:6][C:5]([CH3:37])([C:30]1[CH:31]=[CH:32][C:33]([CH3:36])=[CH:34][CH:35]=1)[C:4]([OH:38])=[O:3])[C:16]([OH:18])=[O:17]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 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., 2H), 7.22 (d, 4H, J=8.1), 7.12 (d, 4H, J=8.1), 2.36 (t, 4H, J=7.5), 2.31 (s, 6H), 1.98-1.80 (m, 4H), 1.56-1.44 (m, 4H), 1.51 (s, 6H), 1.24-1.15 (m, 4H). 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-e35e01249345407c8483301b255feab0
Source dataset
uspto-grants-2007_12
Patent number
US07304093B2

Reaction notes

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