Acetic Acid → Dimethyl (methoxymethyl)succinate

HRID 1462603Notes

Reaction equation

HRID 1462603 reaction equation
[C:1]([O:10][CH3:11])(=[O:9])[C:2]([CH2:4][C:5]([O:7][CH3:8])=[O:6])=[CH2:3].C[O-].[Na+].[C:15](O)(=[O:17])C>CO>[CH3:15][O:17][CH2:3][CH:2]([CH2:4][C:5]([O:7][CH3:8])=[O:6])[C:1]([O:10][CH3:11])=[O:9]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 69240Dimethyl itaconateHCID 10942334Sodium Methoxide

Product 1

HCID 91390Dimethyl (methoxymethyl)succinateYield 80.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

200 g of dimethyl itaconate are dissolved, together with 5.9 g of sodium methoxide, in 650 ml of methanol and the solution is left to stand for four days. The solution is then acidified with acetic acid and fractionally distilled. 240 g (83.4% of the theoretical yield) of dimethyl 2-methoxymethylsuccinate are obtained, at a boiling range of from 109° to 112° C. After the ester has been hydrolyzed with 2N HCl, the free acid is obtained in a yield of 80.3% of the theoretical yield.

Workup

  1. waitthe solution is left
  2. distillationfractionally distilled

Sources & evidence

ORD record
ord-6bc54f5fea5b48e984c7d058a6102fe4
Source dataset
uspto-grants-1984_07
Patent number
US04460782

Reaction notes

Loading…