Sulfuric Acid → Diethyl 2,2-dimethyl-1,3-dioxane-5,5-dicarboxylate

HRID 546162Notes

Reaction equation

HRID 546162 reaction equation
[OH:1][CH2:2][C:3]([CH2:14][OH:15])([C:9]([O:11][CH2:12][CH3:13])=[O:10])[C:4]([O:6][CH2:7][CH3:8])=[O:5].CO[C:18](OC)([CH3:20])[CH3:19].S(=O)(=O)(O)O.C(=O)([O-])[O-].[Na+].[Na+]>CC(C)=O>[CH2:12]([O:11][C:9]([C:3]1([C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH2:2][O:1][C:18]([CH3:20])([CH3:19])[O:15][CH2:14]1)=[O:10])[CH3:13]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 64952,2-DimethoxypropaneHCID 10340Sodium CarbonateHCID 311844Propanedioic acid, 2,2-bis(hydroxymethyl)-, 1,3-diethyl ester

Product 1

HCID 287722Diethyl 2,2-dimethyl-1,3-dioxane-5,5-dicarboxylateYield 91%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Diethyl 2,2-bis(hydroxymethyl)malonate (20 g, 90.82 mmol), acetone (20 ml), 2,2-dimethoxypropane (20 ml), and concentrated sulfuric acid (0.2 ml) were stirred at 25° C. for 2 days. The reaction was slowly poured into saturated aqueous sodium carbonate. The organic supernatant was separated and concentrated in vacuo. The residue was then dissolved in ether, rinsed with saturated aqueous sodium carbonate and brine, and then dried over magnesium sulfate, filtered and concentrated in vacuo to afford crude 2,2-dimethyl-[1,3]dioxane-5,5-dicarboxylic acid diethyl ester (21.4 g, 91%) as a light yellow oil: 1H NMR (300 MHz, CDCl3) δ ppm 1.27 (t, J=7.1 Hz, 6H, 2×CH3), 1.42 (s, 6H, 2×CH3), 4.24 (q, J=7.1 Hz, 4H, 2×OCH2), 4.29 (s, 4H, 2×OCH2).

Workup

  1. customThe organic supernatant was separated
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was then dissolved in ether
  4. washrinsed with saturated aqueous sodium carbonate and brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7e25cf4ea5aa436bbc90900affa94698
Source dataset
uspto-grants-2011_05
Patent number
US07935699B2

Reaction notes

Loading…