Ethyl bromoacetate → Diethyl 2,2'-oxydiacetate

HRID 918267Notes

Reaction equation

HRID 918267 reaction equation
[H-].[Na+].[C:3]([O:7][CH2:8][CH3:9])(=[O:6])[CH2:4][OH:5].Br[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13].O1CC[CH2:19][CH2:18]1>>[C:12]([O:14][CH2:15][CH3:16])(=[O:13])[CH2:11][O:5][CH2:4][C:3]([O:7][CH2:8][CH3:9])=[O:6].[CH2:18]([CH:4]([O:5][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:3]([O:7][CH2:8][CH3:9])=[O:6])[CH3:19]

Participants

6

Reactant 4

HCID 7748Ethyl bromoacetateHCID 8028TetrahydrofuranHCID 12184Ethyl Glycolate2×HCID 24758Sodium hydride

Product 2

HCID 242855Diethyl 2,2'-oxydiacetateHCID 86733712HCID 86733712, compound

Conditions

Temperature
25 °C

Procedure

Diethyl diglycolate is prepared by slurrying 270 parts sodium hydride in 2800 parts tetrahydrofuran and adding 705 parts ethyl glycolate to the mixture while maintaining the temperature between 10° to 15°C. The mixture is stirred for 1 hour at 25°C, cooled to 15°C and 894 parts ethyl bromoacetate is added. The mixture is stirred for 12 hours at 25°C; solvent evaporated; residue washed with water to remove salts; dried and purified diethyl digylcolate recovered by distillation under reduced pressure. (Note: Diethyl methylglycolate or diethyl ethyldiglycolate are prepared by similar procedures wherein ethyl lactate (800 parts) or ethyl-2-hydroxybutyrate (895 parts) are, respectively, substituted for the ethyl glycolate.)

Workup

  1. temperaturewhile maintaining the temperature between 10° to 15°C
  2. temperaturecooled to 15°C
  3. stirringThe mixture is stirred for 12 hours at 25°C
  4. customsolvent evaporated
  5. washresidue washed with water
  6. customto remove salts
  7. customdried
  8. custompurified diethyl digylcolate
  9. distillationrecovered by distillation under reduced pressure

Sources & evidence

ORD record
ord-0e8b887365f344dda23124b10a8d5c72
Source dataset
uspto-grants-1976_07
Patent number
US03970698

Reaction notes

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