Water → 1,3-Propanediol, 2-(2,2-dimethoxyethyl)-

HRID 2291844Notes

Reaction equation

HRID 2291844 reaction equation
[CH3:1][O:2][CH:3]([O:16][CH3:17])[CH2:4][CH:5]([C:11](OCC)=[O:12])[C:6](OCC)=[O:7].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>CCOCC>[CH3:17][O:16][CH:3]([O:2][CH3:1])[CH2:4][CH:5]([CH2:11][OH:12])[CH2:6][OH:7]

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 14215238Diethyl (2,2-dimethoxyethyl)malonateHCID 21226445Aluminium lithium hydride

Product 1

HCID 117895481,3-Propanediol, 2-(2,2-dimethoxyethyl)-Yield 66.5%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Diethyl (2,2-dimethoxyethyl)malonate (115.0 g, 0.46 mol) was added to a suspension of lithium aluminum hydride (38.0 g, 1.00 mol) in 400 ml of dry ether at a rate to maintain a gentle reflux. After stirring for 15 min. 40 ml of water, 40 ml of 15% aqueous NaOH, and 120 ml of water were added and stirring was continued until a white suspension was obtained. The inorganic salts were filtered off and extracted with several 200 ml portions of tetrahydrofuran (THF). The combined organic extracts were evaporated and distilled twice in vacuum to yield 50.23 g (66.5%) of the title compound. B.p. 116°-125° (0.02 mm Hg).

Workup

  1. temperatureto maintain a gentle reflux
  2. stirringstirring
  3. customwas obtained
  4. filtrationThe inorganic salts were filtered off
  5. extractionextracted with several 200 ml portions of tetrahydrofuran (THF)
  6. customThe combined organic extracts were evaporated
  7. distillationdistilled twice in vacuum

Sources & evidence

ORD record
ord-a734558324664f67a0840fe933ae2966
Source dataset
uspto-grants-1989_01
Patent number
US04798833

Reaction notes

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