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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2200822Generated: October 26, 2026

Methyl p-toluenesulfonate → Methyl 3-methoxy-2,2-dimethylpropanoate

https://huagongshe.com/reaction/2200822

Reaction equation

Participants

RoleNameHCIDCharge
ReactantMethyl p-toluenesulfonateHCID 6645—
ReactantSodium hydrideHCID 24758—
ReactantMethyl 3-hydroxypivalateHCID 84152—
SolventDimethylformamideHCID 6228—
SolventWater hexaneHCID 22114717—
ProductMethyl 3-methoxy-2,2-dimethylpropanoateHCID 1430219255%

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 methyl 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 the solution, which was then stirred, after which water was removed therefrom. The resulting organic material was concentrated, and the residue was fractionated at 700 Pa and 93° C., thereby obtaining the intermediate 3-methoxy-2,2-dimethylpropionic acid methyl ester at a yield of 55%.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09359383B2
Source datasetuspto-grants-2016_06
ORD IDord-4391fcca73704781b41fcbedfa8e3e0f
Source noteuspto-grants-2016_06