Ethyl p-methylbenzenesulfonate → Methyl 3-methoxy-2,2-dimethylpropanoate

HRID 2200824Notes

Reaction equation

HRID 2200824 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)C>CN(C)C=O.O.CCCCCC>[CH3:3][O:4][C:5](=[O:11])[C:6]([CH3:10])([CH3:9])[CH2:7][O:8][CH3:12]

Participants

6

Reactant 3

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

Product 1

HCID 14302192Methyl 3-methoxy-2,2-dimethylpropanoateYield 47%

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 under reduced pressure 76-79° C., thereby obtaining the intermediate 3-methoxy-2,2-dimethylpropionic acid methyl ester at a yield of 47%.

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 under reduced pressure 76-79° C.

Sources & evidence

ORD record
ord-deb0200c09524eb59aacdb6307a611ce
Source dataset
uspto-grants-2016_06
Patent number
US09359383B2

Reaction notes

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