Methyl chloroacetate → HCID 85924743, compound

HRID 839425Notes

Reaction equation

HRID 839425 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, compound

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 10.7g (0.1M) p-toluidine, 21.7g (0.2M) methylchloroacetate, 50 ml water, and 80 ml dioxane. The solution was heated to reflux and 32g of an aqueous solution containing 8g (0.2M) 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 24.6g 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-ea8fdfc88fdb49cb8925f91dfa741949
Source dataset
uspto-grants-1978_06
Patent number
US04095019

Reaction notes

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