Ethanol → 2,2-Bis(6-hydroxy-5,5-dimethylhexyl)malonic acid diethyl ester

HRID 873267Notes

Reaction equation

HRID 873267 reaction equation
[CH2:1]([O:3][C:4](=[O:41])[C:5]([CH2:26][CH2:27][CH2:28][CH2:29][C:30]([CH3:40])([CH3:39])[CH2:31][O:32]C1CCCCO1)([CH2:11][CH2:12][CH2:13][CH2:14][C:15]([CH3:25])([CH3:24])[CH2:16][O:17]C1CCCCO1)[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH3:2].C(O)C>Cl.O>[CH2:9]([O:8][C:6](=[O:7])[C:5]([CH2:26][CH2:27][CH2:28][CH2:29][C:30]([CH3:39])([CH3:40])[CH2:31][OH:32])([CH2:11][CH2:12][CH2:13][CH2:14][C:15]([CH3:24])([CH3:25])[CH2:16][OH:17])[C:4]([O:3][CH2:1][CH3:2])=[O:41])[CH3:10]

Participants

5

Reactant 2

HCID 702EthanolHCID 117069512,2-Bis[5,5-dimethyl-6-(tetrahydropyran-2-yloxy)-hexyl]malonic acid diethyl ester

Product 1

HCID 117043932,2-Bis(6-hydroxy-5,5-dimethylhexyl)malonic acid diethyl esterYield 84%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent2×

Procedure

A solution of 2,2-bis-[5,5-dimethyl-6-(tetrahydropyran-2-yloxy)-hexyl]-malonic acid diethyl ester (2.92 g, 5 mmol) in concentrated HCl (2.4 mL) and water (1.6 mL) was refluxed for 1 h. Ethanol (8.2 mL) was added and the reaction mixture was heated to reflux for 3 h. The reaction mixture was diluted with water (20 mL) and extracted with diethyl ether (3×20 mL). The combined organic layers were washed with water (20 mL), brine (20 mL), and dried over Na2SO4. The solution was concentrated to furnish 2,2-bis(6-hydroxy-5,5-dimethyl-hexyl)-malonic acid diethyl ester (1.74 g, 84%). 1H NMR (300 MHz, CDCl3/TMS): (ppm) 4.13 (q, J=7.2 Hz, 4H), 3.25 (s, 4H), 2.42 (s, 2H), 1.90-1.75 (m, 4H), 1.30-1.12 (m, 18H), 0.84 (s, 12H). 13C NMR (75 MHz, CDCl3/TMS): (ppm) 172.0, 71.7, 60.9, 57.4, 38.2, 34.9, 32.1, 24.8, 24.0, 23.7, 14.0.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux for 3 h
  3. extractionextracted with diethyl ether (3×20 mL)
  4. washThe combined organic layers were washed with water (20 mL), brine (20 mL)
  5. dry with materialdried over Na2SO4
  6. concentrationThe solution was concentrated

Sources & evidence

ORD record
ord-61a156137c3e488b9e7083c19e7570a6
Source dataset
uspto-grants-2015_03
Patent number
US08975300B2

Reaction notes

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