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

HRID 646799Notes

Reaction equation

HRID 646799 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 82.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a stirred solution of KOH (4.83 g, 75 mmol) in water (4.2 mL) and ethanol (15 mL) was added 2,2-bis(6-hydroxy-5,5-dimethyl-hexyl)-malonic acid diethyl ester (15 g). The reaction mixture was heated to reflux for 14 h, then concentrated in vacuo, and extracted with chloroform. The aqueous layer was acidified with HCl until pH 1 and extracted with diethyl ether (3×50 mL). The ethereal solution was dried over anhydrous MgSO4 and concentrated in vacuo to afford get 2,2-bis-(6-hydroxy-5,5-dimethyl-hexyl)-malonic acid (7.8 g, 82.3%) as a yellow solid. 1H NMR (300 MHz, CD3OD/TMS): (ppm) 4.86 (s, 4H), 3.22 (s, 4H), 1.9-1.8 (m, 4H), 1.36-1.10 (m, 12H), 0.84 (s, 12H). 13C NMR (75 MHz, CD3OD/TMS): (ppm) 176.0, 72.0, 58.7, 39.8, 36.0, 34.1, 26.5, 25.5, 24.5. Mp.: 178-180 C.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 14 h
  3. concentrationconcentrated in vacuo
  4. extractionextracted with chloroform
  5. extractionextracted with diethyl ether (3×50 mL)
  6. dry with materialThe ethereal solution was dried over anhydrous MgSO4
  7. concentrationconcentrated in vacuo
  8. customto afford

Sources & evidence

ORD record
ord-36f199d11c55464b86363b1d5cca888f
Source dataset
uspto-grants-2010_04
Patent number
US07705177B2

Reaction notes

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