Methyl chloroacetate → HCID 85924743, compound

HRID 1448928Notes

Reaction equation

HRID 1448928 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][CH:3]=1.[CH3:9][O:10][C:11](=[O:14])[CH2:12]Cl.[OH-:15].[Na+]>O.O1CCOCC1>[CH3:9][O:10][C:11](=[O:14])[CH2:12][N:1]([CH2:12][C:11]([O:10][CH3:9])=[O:15])[C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 7295Methyl chloroacetateHCID 7813p-ToluidineHCID 14798Sodium Hydroxide

Product 1

HCID 85924743HCID 85924743, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Conditions

Temperature
5 °C

Procedure

Into a three-neck r.b. flask, fitted with stirring assembly, thermometer, reflux condenser, and a dropping funnel were placed 10.7 g (0.1 M) p-toluidine, 21.7 g (0.2 M) methylchloroacetate, 50 ml water, and 80 ml dioxane. The solution was heated to reflux and 32 g of an aqueous solution containing 8 g (0.2 M) sodium hydroxide was added dropwise so as to maintain the charge at a neutral pH. Addition was completed within 11/2 hours. The flask was cooled to 5° C., and the product was poured into a 4 l. beaker. Upon addition of 3 l. of water, a ppt. formed which was discarded. Extraction of the aqueous phase with chloroform and stripping the extract gave 24.6 g of light-yellow solid.

Workup

  1. customflask, fitted
  2. temperaturethermometer, reflux condenser, and a dropping funnel
  3. temperatureThe solution was heated
  4. temperatureto reflux
  5. additionwas added dropwise so as
  6. temperatureto maintain the
  7. additioncharge at a neutral pH
  8. additionAddition
  9. custom2 hours
  10. additionthe product was poured into a 4 l
  11. additionUpon addition of 3 l
  12. customformed which
  13. extractionExtraction of the aqueous phase with chloroform

Sources & evidence

ORD record
ord-71d4e455adc548a3aa2954d60b6518df
Source dataset
uspto-grants-1980_02
Patent number
US04188349

Reaction notes

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