Sodium Sulfate → 2,2-diethoxypropan-1-ol

HRID 537649Notes

Reaction equation

HRID 537649 reaction equation
[CH2:1]([O:3][C:4]([O:11][CH2:12][CH3:13])([CH3:10])[C:5](OCC)=[O:6])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].S([O-])([O-])(=O)=O.[Na+].[Na+]>C(OCC)C>[CH2:1]([O:3][C:4]([O:11][CH2:12][CH3:13])([CH3:10])[CH2:5][OH:6])[CH3:2]

Participants

5

Reactant 3

HCID 24436Sodium SulfateHCID 95835Propionic acid, 2,2-diethoxy-, ethyl esterHCID 21226445Aluminium lithium hydride

Product 1

HCID 117010602,2-diethoxypropan-1-olYield 76.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of ethyl pyruvate diethyl ketal (16.0 g, 0.084 moles) in ethyl ether (60 mL) was added dropwise during 30 min to a stirred solution of lithium aluminum hydride (1.90 g, 0.050 moles) in ethyl ether (150 mL). Next the mixture was stirred 1 h at room temperature under nitrogen atmosphere. Saturated solution of sodium sulfate (20 mL) was added and the mixture was stirred 15 min. Next the mixture was filtered, dried with anhydrous magnesium sulfate, and the solvent was distilled off. The residue was subjected to fractional vacuum distillation giving 9.5 g of pure 2,2-diethoxypropan-1-ol. NMR (d6-DMSO): 1.17 ppm (t, —CH3, ethyl (ketal), 6H), 1.31 ppm (s, —CH3—C—CH2OH, 3H), 3.37 ppm (q, —OCH2CH3, (ketal), 4H), 3.86 ppm (d, —CH2OH, 2H), 4.45 ppm (t, —OH, 1H).

Workup

  1. stirringthe mixture was stirred 15 min
  2. filtrationNext the mixture was filtered
  3. dry with materialdried with anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off
  5. distillationThe residue was subjected to fractional vacuum distillation

Sources & evidence

ORD record
ord-6e36eb88216f4ce7a65a4a550bf39111
Source dataset
uspto-grants-2014_10
Patent number
US08865149B2

Reaction notes

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