Ethanol → Ethyl 2,2-dimethyl-1,3-dioxane-5-carboxylate

HRID 1074881Notes

Reaction equation

HRID 1074881 reaction equation
[CH3:1][C:2]1([CH3:18])[O:7][CH2:6][C:5](C(OCC)=O)([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:4][O:3]1.[Cl-].[Na+].O.C(O)C>CS(C)=O>[CH3:1][C:2]1([CH3:18])[O:3][CH2:4][CH:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:6][O:7]1

Participants

6

Reactant 4

HCID 702EthanolHCID 962Water2×HCID 5234Sodium ChlorideHCID 287722Diethyl 2,2-dimethyl-1,3-dioxane-5,5-dicarboxylate

Product 1

HCID 11019611Ethyl 2,2-dimethyl-1,3-dioxane-5-carboxylateYield 57%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
180 °C

Procedure

To a solution of the product of Example 2 (65 g) in dimethyl sulfoxide (65 g) is added sodium chloride (1 g). The mixture is stirred while warming at about 180° C., and water is added in small portions while maintaining the temperature between 170° and 180°. Ethanol and water are evolved and are removed by distillation until about 60 ml of liquid has been collected. The mixture is cooled, ether (200 ml) added, and the mixture partitioned with 3 portions of water (50 ml). The organic phase is dried over sodium sulfate and evaporated to a residue. Distillation of the residue gives the title product (25 g) (57%) B.P. 38° (0.01 mm) nD26 1.4400.

Workup

  1. temperaturewhile maintaining the temperature between 170° and 180°
  2. customare removed by distillation until about 60 ml of liquid
  3. customhas been collected
  4. temperatureThe mixture is cooled
  5. additionether (200 ml) added
  6. customthe mixture partitioned with 3 portions of water (50 ml)
  7. dry with materialThe organic phase is dried over sodium sulfate
  8. customevaporated to a residue
  9. distillationDistillation of the residue

Sources & evidence

ORD record
ord-6e62efbb986a41a99fb73a869d3e7c6b
Source dataset
uspto-grants-1983_07
Patent number
US04394329

Reaction notes

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