Ethanol → Diethyl 2,2'-(1,2-phenylene)diacetate

HRID 539863Notes

Reaction equation

HRID 539863 reaction equation
[C:1]1([CH2:10][C:11]#N)[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1CC#N.S(=O)(=O)(O)O.[OH-:18].[NH4+].[C:20]([O:23][C:24](=[O:26])[CH3:25])(=O)[CH3:21].[CH2:27]([OH:29])[CH3:28]>CCCCCC>[CH2:27]([O:29][C:11](=[O:18])[CH2:10][C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][C:6]=1[CH2:25][C:24]([O:23][CH2:20][CH3:21])=[O:26])[CH3:28]

Participants

7

Reactant 5

HCID 702EthanolHCID 1118Sulfuric AcidHCID 7918Acetic AnhydrideHCID 14923Ammonium HydroxideHCID 69180o-Phenylenediacetonitrile

Product 1

HCID 12427121Diethyl 2,2'-(1,2-phenylene)diacetate

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

1,2-phenylenediacetonitrile (1.0 g, 6.40 mmol) was dissolved in 5 ml ethyl alcohol and 2 ml concentrated sulfuric acid in a 25 ml round bottom flask. The mixture was stirred and heated to reflux for 6 hours. After neutralizing the reaction solution with ammonium hydroxide, the result solution was extracted with ethyl acetate (3×50 ml). The organic phase was combined and dried with Na2SO4. Concentration of the ethyl acetate afforded a yellow liquid. Running column with hexane: acetyl acetate=10:1, got yellow liquid 1.13 g (70.6%). 1H NMR (DMSO-d6): δ 1.24(t, 6H, CH3), δ 3.7 (s, 4H, CH2CO), δ 4.16(q, 4H, OCH2), δ 7.3 (d, 4H, Ar—H).

Workup

  1. temperatureheated
  2. temperatureto reflux for 6 hours
  3. extractionthe result solution was extracted with ethyl acetate (3×50 ml)
  4. dry with materialdried with Na2SO4
  5. customConcentration of the ethyl acetate afforded a yellow liquid

Sources & evidence

ORD record
ord-230d734293e64b519f2325f6ea35b38e
Source dataset
uspto-grants-2014_10
Patent number
US08871776B2

Reaction notes

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