Methanol → HCID 11287403, compound

HRID 1265399Notes

Reaction equation

HRID 1265399 reaction equation
[C:1]([O:6][CH3:7])(=[O:5])[CH:2]([CH3:4])[OH:3].[C:8]1(=[O:14])[O:13][C:11](=[O:12])[CH2:10][CH2:9]1.CO.[C:17]([O-])([O-])=O.[Ca+2]>S(=O)(=O)(O)O.C(Cl)(Cl)Cl>[CH3:17][O:13][C:11](=[O:12])[CH2:10][CH2:9][C:8]([O:3][CH:2]([C:1]([O:6][CH3:7])=[O:5])[CH3:4])=[O:14]

Participants

7

Reactant 4

HCID 887MethanolHCID 7922Succinic anhydrideHCID 10112Calcium CarbonateHCID 11040Methyl Lactate

Product 1

HCID 11287403HCID 11287403, compound

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 6212ChloroformSolvent

Conditions

Temperature
70 °C

Procedure

Methyl lactate (14 mL, 0.147 moles), succinic anhydride (14.76 g, 0.147 moles), and 2 drops of concentrated sulfuric acid were mixed and heated to 70° C. for five hours. An NMR spectrum of a sample of the cooled reaction mixture showed quantitative conversion to succinic acid (ethyl-1-methoxycarbonyl) ester. Methanol (30 mL) and chloroform (20 mL) were added and heated to reflux in a soxhlet extractor containing silica gel in the receiver. The solution was refluxed for three hours, neutralized with CaCO3, filtered, and the volatile solvents removed under vacuum. The isolated yield of (i) was 29.56 g (98.5%).

Workup

  1. customAn NMR spectrum of a sample of the cooled reaction mixture
  2. temperatureheated
  3. temperatureto reflux in a soxhlet extractor
  4. additioncontaining silica gel in the receiver
  5. temperatureThe solution was refluxed for three hours
  6. filtrationfiltered
  7. customthe volatile solvents removed under vacuum

Sources & evidence

ORD record
ord-7406d3e57b87463e9954cf6936325c90
Source dataset
uspto-grants-2003_04
Patent number
US06545175B1

Reaction notes

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