Potassium Hydroxide → 2,2-Bis(6-hydroxy-5,5-dimethylhexyl)malonic acid

HRID 1159702Notes

Reaction equation

HRID 1159702 reaction equation
[OH-].[K+].C([O:5][C:6](=[O:31])[C:7]([CH2:22][CH2:23][CH2:24][CH2:25][C:26]([CH3:30])([CH3:29])[CH2:27][OH:28])([CH2:13][CH2:14][CH2:15][CH2:16][C:17]([CH3:21])([CH3:20])[CH2:18][OH:19])[C:8]([O:10]CC)=[O:9])C>O.C(O)C>[OH:28][CH2:27][C:26]([CH3:30])([CH3:29])[CH2:25][CH2:24][CH2:23][CH2:22][C:7]([CH2:13][CH2:14][CH2:15][CH2:16][C:17]([CH3:21])([CH3:20])[CH2:18][OH:19])([C:8]([OH:10])=[O:9])[C:6]([OH:31])=[O:5]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 117043932,2-Bis(6-hydroxy-5,5-dimethylhexyl)malonic acid diethyl ester

Product 1

HCID 116749172,2-Bis(6-hydroxy-5,5-dimethylhexyl)malonic acidYield 82%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a stirred solution of potassium hydroxide (4.83 g, 75 mmol) in water (4.2 mL) and ethanol (15 mL) was added 2,2-bis(6-hydroxy-5,5-dimethylhexyl)malonic acid diethyl ester (15.0 g). The reaction mixture was heated at reflux for 14 h. The ethanol was removed under reduced pressure and the aqueous solution was extracted with chloroform (2×50 mL). The aqueous layer was acidified with hydrochloric acid to pH 1 and extracted with diethyl ether (3×50 mL). The ethereal phases were dried over magnesium sulfate and concentrated in vacuo to yield 2,2-bis(6-hydroxy-5,5-dimethylhexyl)malonic acid (7.8 g, 82%) as a yellow solid. M.P.: 178-180° C. 1H NMR (300 MHz, CD3OD/TMS): δ (ppm): 4.86 (s br., 4 H), 3.22 (s, 4 H), 1.9-1.8 (m, 4 H), 1.36-1.10 (m, 12 H), 0.84 (s, 12 H). 13C NMR (75 MHz, CD3OD/TMS): δ (ppm): 176.0, 72.0, 58.7, 39.8, 36.0, 34.1, 26.5, 25.5, 24.5. HRMS (LSIMS, gly): Calcd. for C19H37O6 (MH+): 361.2590, found: 361.2582.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 14 h
  3. customThe ethanol was removed under reduced pressure
  4. extractionthe aqueous solution was extracted with chloroform (2×50 mL)
  5. extractionextracted with diethyl ether (3×50 mL)
  6. dry with materialThe ethereal phases were dried over magnesium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-131bd91b29b447c2841b2f355d23757f
Source dataset
uspto-grants-2010_10
Patent number
US07812199B2

Reaction notes

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