Carbon Dioxide → HCID 20378053, compound

HRID 2051747Notes

Reaction equation

HRID 2051747 reaction equation
[C:1]([O:5][CH3:6])(=[O:4])[CH:2]=[O:3].Br[CH:8]([CH2:13][OH:14])[C:9]([O:11][CH3:12])=[O:10].C(=O)([O-])[O-].[K+].[K+].C(=O)=O>CCCCCC>[O:14]1[CH2:13][CH:8]([C:9]([O:11][CH3:12])=[O:10])[O:3][CH:2]1[C:1]([O:5][CH3:6])=[O:4]

Participants

6

Reactant 4

HCID 280Carbon DioxideHCID 11430Potassium CarbonateHCID 70205Acetic acid, 2-oxo-, methyl esterHCID 11964350methyl 2-bromo-3-hydroxypropionate

Product 1

HCID 20378053HCID 20378053, compoundYield 21.4%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

Methyl glyoxylate 11.3 g (0.128 mol) and methyl 2-bromo-3-hydroxypropionate 31 g (0.129 mol) were mixed and the mildly exothermic reaction allowed to cool. The mixture was then treated with hexane (50 ml) and 17.8 g (0.129 mol) potassium carbonate. Evolution of CO2 was sluggish; the mixture was warmed to 45° and allowed to stir overnight. The work-up as described in Example 1 yielded after ether removal, 13.0 g of a light yellow liquid. Distillation in vacuo gave 5.2 g (21%) of the title compound bp 84°-86° at 0.3 mm Hg as a clear colorless liquid. Analysis by GlPC indicated >96% purity, and the pmr spectrum indicated a mixture of trans & cis isomers approximately 70-80% trans.

Workup

  1. customthe mildly exothermic reaction
  2. temperatureto cool
  3. temperaturethe mixture was warmed to 45°
  4. customyielded
  5. customafter ether removal, 13.0 g of a light yellow liquid
  6. distillationDistillation in vacuo

Sources & evidence

ORD record
ord-07ad29f2c02e49ba85fd2f8e96b54afa
Source dataset
uspto-grants-1980_01
Patent number
US04182718

Reaction notes

Loading…