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

HRID 969019Notes

Reaction equation

HRID 969019 reaction equation
C([O:3][C:4](=[O:28])[C:5]([CH3:27])([CH3:26])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11](=[O:25])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([CH3:24])([CH3:23])[C:18]([O:20]CC)=[O:19])C.[OH-].[K+]>C(O)C.O>[CH3:23][C:17]([CH3:24])([CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][C:11](=[O:25])[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][C:5]([CH3:27])([CH3:26])[C:4]([OH:28])=[O:3])[C:18]([OH:20])=[O:19]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 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, 8H), 1.30-1.20 (m, 8H), 1.18 (s, 12H). 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-899b06547c394d79a2fe30efe1d0e63d
Source dataset
uspto-grants-2007_12
Patent number
US07304093B2

Reaction notes

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