Ethyl Lactate → Ethyl 2-[(1'-ethoxy)propoxy]propanoate

HRID 2231147Notes

Reaction equation

HRID 2231147 reaction equation
[C:1]([O:6][CH2:7][CH3:8])(=[O:5])[CH:2]([CH3:4])[OH:3].[CH:9]([O:12][CH2:13][CH3:14])=[CH:10][CH3:11]>Cl>[CH2:13]([O:12][CH:9]([O:3][CH:2]([CH3:4])[C:1]([O:6][CH2:7][CH3:8])=[O:5])[CH2:10][CH3:11])[CH3:14]

Participants

4

Reactant 2

HCID 7344Ethyl LactateHCID 13570Ethyl 1-propenyl ether

Product 1

HCID 21286133Ethyl 2-[(1'-ethoxy)propoxy]propanoateYield 90%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidCatalyst

Conditions

Temperature
75 °C

Procedure

To a 250 mL containing 37.0 g (0.31 mole) ethyl lactate and four drops 32% hydrochloric acid at 30° C. is added 71 g (0.82 mole) ethyl propenyl ether. The mixture is heated to 75° C. for thirty minutes, cooled to 25° C., then quenched with 100 g 5% sodium bicarbonate solution. The organic material was flash distilled yielding 52.3 g (90%) ethyl 2-[(1'-ethoxy)propoxy]propanoate.

Workup

  1. temperaturecooled to 25° C.
  2. customquenched with 100 g 5% sodium bicarbonate solution
  3. distillationdistilled

Sources & evidence

ORD record
ord-98e861ada03a43d081079ee25407b106
Source dataset
uspto-grants-1988_11
Patent number
US04781762

Reaction notes

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