Hydrochloric Acid → Dimethyl methoxymethylenemalonate

HRID 978793Notes

Reaction equation

HRID 978793 reaction equation
[CH3:1][O:2][C:3](=[O:11])[C:4](=[CH:9][OH:10])[C:5]([O:7][CH3:8])=[O:6].CO.Cl.[C:15](#N)C>>[CH3:8][O:7][C:5](=[O:6])[C:4](=[CH:9][O:10][CH3:15])[C:3]([O:2][CH3:1])=[O:11]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 6342AcetonitrileHCID 119754Dimethyl (hydroxymethylene)malonate

Product 1

HCID 90770Dimethyl methoxymethylenemalonateYield 79%

Procedure

160 g (1.0 mol) of hydroxymethylenemalonic acid dimethyl ester is dissolved in 288 g (9.0 mol) of methanol and 50 g of hydrogen chloride gas is introduced. Then 55.2 g (1.35 mol) of acetonitrile is added and the mixture is let stand for 24 hours at room temperature. Then the low-boiling substances are distilled out, dichloromethane is added to the residue, and ammonium chloride is filtered out. The filtrate is treated with 1.6 g of potassium bisulfate and heated while distilling the volatile components up to 130° C. 138 g (0.79 mol) of methoxymethylenmalonic acid dimethyl ester is obtained, corresponding to 79.3% of the theory.

Workup

  1. distillationThen the low-boiling substances are distilled out
  2. additiondichloromethane is added to the residue, and ammonium chloride
  3. filtrationis filtered out
  4. additionThe filtrate is treated with 1.6 g of potassium bisulfate
  5. temperatureheated
  6. distillationwhile distilling the volatile components up to 130° C

Sources & evidence

ORD record
ord-10314745084d43c7a7a9eaed9b7a7a6c
Source dataset
uspto-grants-1987_05
Patent number
US04665218

Reaction notes

Loading…