Ethylene Glycol → 2-Hydroxyethyl N-methyl-N-phenylglycinate

HRID 1105776

Reaction equation

HRID 1105776 reaction equation
[CH2:1]([OH:4])[CH2:2][OH:3].[CH3:5][N:6]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:7][C:8](OCC)=[O:9].C[O-].[Na+].Cl>O>[CH3:5][N:6]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:7][C:8]([O:3][CH2:2][CH2:1][OH:4])=[O:9]

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 313Hydrochloric AcidHCID 265936(Methyl-phenyl-amino)-acetic acid ethyl esterHCID 10942334Sodium Methoxide

Product 1

HCID 205549612-Hydroxyethyl N-methyl-N-phenylglycinate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

Into a 100 ml. flask fitted with a condenser and a Dean-Stark trap there were placed 49.5 gms. ethylene glycol, 17 gms. of ethyl N-methyl-N-phenylglycinate and 0.7 gm. sodium methoxide. The flask and contents were heated to 150° C. in an oil bath and stirred for 13 hours. The reaction mixture was allowed to cool to room temperature and 1.25 ml. of concentrated HCl in 3.5 ml. water were added and the mixture was stirred for 10 minutes. After the ethylene glycol was distilled off at atmospheric pressure, 11.5 gms. of product was obtained by vacuum distillation, b.p. (0.3 mm.) 139°-149° C.

Workup

  1. customflask fitted with a condenser
  2. temperatureto cool to room temperature
  3. stirringthe mixture was stirred for 10 minutes
  4. distillationAfter the ethylene glycol was distilled off at atmospheric pressure, 11.5 gms
  5. customof product was obtained by vacuum distillation, b.p
  6. custom(0.3 mm.) 139°-149° C.

Sources & evidence

ORD record
ord-a42ba69b9911477aacbdbc293192e764
Source dataset
uspto-grants-1982_01
Patent number
US04310512

Linked notes

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