Ethyl Acetate → HCID 67081917, compound

HRID 2273554Notes

Reaction equation

HRID 2273554 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][O:8][C:9]1[CH:10]=[C:11]([O:22][CH2:23][C:24](OCC)=[O:25])[CH:12]=[C:13]([O:15][CH2:16][C:17](OCC)=[O:18])[CH:14]=1.C(OCC)(=O)C.S([O-])(O)(=O)=O.[K+]>O1CCCC1>[CH3:7][O:8][C:9]1[CH:14]=[C:13]([O:15][CH2:16][CH2:17][OH:18])[CH:12]=[C:11]([O:22][CH2:23][CH2:24][OH:25])[CH:10]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 516920Potassium bisulfateHCID 21226445Aluminium lithium hydrideHCID 67081820HCID 67081820, compound

Product 1

HCID 67081917HCID 67081917, compoundYield 136.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

10 ml of lithium aluminium hydride (1 M in tetrahydrofuran) are introduced into a three-necked flask under argon. After having cooled the solution to 0° C., 1.0 g (3.2 mmol) of diethyl 2,2′-[(5-methoxy-1,3-phenylene)bis(oxy)]diacetate in solution in 6 ml of tetrahydrofuran is added. The formation of a white precipitate is observed. After stirring for one hour at ambient temperature, ethyl acetate is slowly added at 0° C. The mixture is poured into a saturated aqueous solution of potassium hydrogen sulphate and the mixture is extracted with ethyl acetate. The organic phase is washed with a saturated solution of sodium chloride and dried over sodium sulphate, then concentrated to dryness. 1.0 g (78%) of a white powder is obtained.

Workup

  1. extractionthe mixture is extracted with ethyl acetate
  2. washThe organic phase is washed with a saturated solution of sodium chloride
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-afd6c3c6703444c18ed2f937dc693a5d
Source dataset
uspto-grants-2015_09
Patent number
US09120819B2

Reaction notes

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