Potassium Hydroxide → 2,2,14,14-Tetramethyl-8-oxopentadecanedioic acid

HRID 239061Notes

Reaction equation

HRID 239061 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:68])[C:45]([CH3:67])([CH3:66])[CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][C:51](=[O:65])[CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][C:57]([CH3:64])([CH3:63])[C:58]([O:60]CC)=[O:59])C.[OH-].[K+]>C(O)C.O>[CH3:63][C:57]([CH3:64])([CH2:56][CH2:55][CH2:54][CH2:53][CH2:52][C:51](=[O:65])[CH2:50][CH2:49][CH2:48][CH2:47][CH2:46][C:45]([CH3:67])([CH3:66])[C:44]([OH:68])=[O:43])[C:58]([OH:60])=[O:59]

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 103252762,12-Bis-(4-isobutylphenyl)-2,12-dimethyl-7-oxotridecanedioic acidHCID 112232782,2,14,14-Tetramethyl-8-oxopentadecanedioic acid diethyl ester

Product 1

HCID 113368222,2,14,14-Tetramethyl-8-oxopentadecanedioic acidYield 57%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

According to the procedure given for 210f, 209g (8.54 g, 21.4 mmol) was saponified with KOH (85%, 4.53 g, 68.6 mmol) in ethanol (13 mL) and water (5 mL) at reflux for 4 h. The solid product obtained after usual workup was recrystallized from Et2O/hexanes (50 mL/50 mL), affording 210g (4.16 g, 57%) as colorless needles. Mp 82-83° C. 1H NMR (CDCl3): δ 11.53 (br., 2H), 2.39 (t, 4H, J=7.3), 1.60-1.50 (m, 8 H), 1.30-1.20 (m, 8 H), 1.18 (s, 12 H). 13C NMR (CDCl3): δ 211.7, 185.0, 42.8, 42.3, 40.4, 29.7, 25.1, 24.8, 23.8. HRMS (LSIMS, gly): Calcd for C19H35O5 (MH+): 343.2484, found: 343.2444. HPLC: 92.6% pure. Anal. (C19H34O5) C, H.

Workup

  1. temperatureat reflux for 4 h
  2. customThe solid product obtained after usual workup
  3. customwas recrystallized from Et2O/hexanes (50 mL/50 mL)

Sources & evidence

ORD record
ord-d63a17cf794b481cbe17babfe855ae77
Source dataset
uspto-grants-2014_02
Patent number
US08642653B2

Reaction notes

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