2,2-Dimethoxypropane → 2,2,5-trimethyl-1,3-dioxane-5-carboxylic Acid

HRID 2037186Notes

Reaction equation

HRID 2037186 reaction equation
[OH:1][CH2:2][C:3]([CH2:8][OH:9])([CH3:7])[C:4]([OH:6])=[O:5].CO[C:12](OC)([CH3:14])[CH3:13]>O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)(O)[O-].[Na+].CC(C)=O>[CH3:13][C:12]1([CH3:14])[O:9][CH2:8][C:3]([CH3:7])([C:4]([OH:6])=[O:5])[CH2:2][O:1]1

Participants

6

Reactant 2

HCID 64952,2-DimethoxypropaneHCID 78501Dimethylolpropionic acid

Product 1

HCID 113557762,2,5-trimethyl-1,3-dioxane-5-carboxylic AcidYield 90.4%

Reagents, catalysts & solvents 3

HCID 516892Sodium BicarbonateCatalystHCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 180AcetoneSolvent

Procedure

To a mixture of 3-hydroxy-2-hydroxymethyl-2-methylpropionic acid (6.71 g, 50 mmol), dimethoxypropane (7.99 mL, 65 mmol) and acetone (50 mL), p-toluenesulfonic acid hydrate (0.048 g, 0.25 mmol) was added and the resulting mixture was stirred at room temperature for 2.5 hours. After the reaction was completed, sodium bicarbonate (0.1 g) was added to the reaction mixture, and the resulting mixture was stirred at room temperature for 5 minutes and concentrated in vacuo. To the resulting residue was added water and the resulting mixture was extracted with ethyl ether. The extract was dried over anhydrous sodium sulphate and concentrated in vacuo to give 2,2,5-trimethyl-1,3-dioxane5-carboxylic acid (7.87 g, yield: 90%) as colorless oil.

Workup

  1. additionwas added
  2. stirringthe resulting mixture was stirred at room temperature for 5 minutes
  3. concentrationconcentrated in vacuo
  4. additionTo the resulting residue was added water
  5. extractionthe resulting mixture was extracted with ethyl ether
  6. dry with materialThe extract was dried over anhydrous sodium sulphate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-cf0d419b82464c6abce57f4ef5fa3653
Source dataset
uspto-grants-2013_11
Patent number
US08575197B2

Reaction notes

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