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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2200823Generated: October 26, 2026

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

https://huagongshe.com/reaction/2200823

Reaction equation

Participants

RoleNameHCIDCharge
ReactantEthyl p-methylbenzenesulfonateHCID 6638—
ReactantSodium hydrideHCID 24758—
ReactantMethyl 3-hydroxypivalateHCID 84152—
SolventDimethylformamideHCID 6228—
SolventWater hexaneHCID 22114717—
Product3-Ethoxy-2,2-dimethylpropionic acid methyl esterHCID 5926801434%

Reaction Steps

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%.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09359383B2
Source datasetuspto-grants-2016_06
ORD IDord-95ccd32d7fb6498c850c7df636ae652b
Source noteuspto-grants-2016_06