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

HRID 2200782Notes

Reaction equation

HRID 2200782 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5](=[O:11])[C:6]([CH3:10])([CH3:9])[CH2:7][OH:8].[CH3:12]OS(C1C=CC(C)=CC=1)(=O)=O>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 6645Methyl p-toluenesulfonateHCID 24758Sodium hydrideHCID 84152Methyl 3-hydroxypivalate

Product 1

HCID 14302192Methyl 3-methoxy-2,2-dimethylpropanoateYield 55%

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 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%.

Workup

  1. additionwas added
  2. customdid not exceed 30° C
  3. customdid not exceed 30° C
  4. additionwas added to the solution, which
  5. stirringwas then stirred
  6. customafter which water was removed
  7. concentrationThe resulting organic material was concentrated
  8. customwas fractionated at 700 Pa and 93° C.

Sources & evidence

ORD record
ord-a700052db35540898656302579f9bcee
Source dataset
uspto-grants-2016_06
Patent number
US09359382B2

Reaction notes

Loading…