Ethyl p-methylbenzenesulfonate → 3-Ethoxy-2,2-dimethylpropionic acid methyl ester

HRID 2200823Notes

Reaction equation

HRID 2200823 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5](=[O:11])[C:6]([CH3:10])([CH3:9])[CH2:7][OH:8].[CH2:12](OS(C1C=CC(C)=CC=1)(=O)=O)[CH3:13]>CN(C)C=O.O.CCCCCC>[CH3:3][O:4][C:5](=[O:11])[C:6]([CH3:10])([CH3:9])[CH2:7][O:8][CH2:12][CH3:13]

Participants

6

Reactant 3

HCID 6638Ethyl p-methylbenzenesulfonateHCID 24758Sodium hydrideHCID 84152Methyl 3-hydroxypivalate

Product 1

HCID 592680143-Ethoxy-2,2-dimethylpropionic acid methyl esterYield 34%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 22114717Water hexaneSolvent

Procedure

1 mol of sodium hydride was added to the solvent dimethylformamide, and 1 mol of hydroxypivalic acid methyl ester was added thereto while the temperature of the solution did not exceed 30° C. The solution was stirred at room temperature for 90 minutes. Then, 1.2 mol of p-toluenesulfonic acid ethyl ester was added to the solution while the temperature of the solution did not exceed 30° C. Then, a water/hexane mixture having the same mass as that of the dimethylformamide was added to and mixed with the solution, after which water was removed therefrom. The resulting organic material was concentrated, and the residue was fractionated at atmospheric pressure and 108-111° C., thereby obtaining the intermediate 3-ethoxy-2,2-dimethylpropionic acid methyl ester at a yield of 34%.

Workup

  1. additionwas added
  2. customdid not exceed 30° C
  3. customdid not exceed 30° C
  4. additionwas added to and
  5. additionmixed with the solution
  6. customafter which water was removed
  7. concentrationThe resulting organic material was concentrated
  8. customwas fractionated at atmospheric pressure and 108-111° C.

Sources & evidence

ORD record
ord-95ccd32d7fb6498c850c7df636ae652b
Source dataset
uspto-grants-2016_06
Patent number
US09359383B2

Reaction notes

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