Ethanol → Diethyl diphenate

HRID 132730Notes

Reaction equation

HRID 132730 reaction equation
[C:1]12[C:13]3=[CH:14][CH:15]=[CH:16][CH:17]=[C:12]3[C:10](=[O:11])[O:9][C:7](=[O:8])[C:2]1=[CH:3][CH:4]=[CH:5][CH:6]=2.[CH2:18](O)[CH3:19].[C:21]1([CH3:27])C=CC=CC=1.S(=O)(=O)(O)[OH:29]>O>[C:13]1([C:1]2[C:2]([C:7]([O:8][CH2:18][CH3:19])=[O:29])=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:12]([C:10]([O:9][CH2:21][CH3:27])=[O:11])=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 1118Sulfuric AcidHCID 1140TolueneHCID 72794Diphenic anhydride

Product 1

HCID 13793399Diethyl diphenateYield 90%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 0.1 mol 2,2′-biphenyl dicarboxylic acid anhydride were added 0.3 mol ethanol, 40 ml toluene, and 0.4 ml concentrated sulfuric acid with stirring. Then the reaction mixture was heated refluxing and the water produced was removed by using a water separator until the amount of the water separated reached theoretical value. Upon the reaction completion, the mixture was neutralized with saturated sodium carbonate solution and extracted with ethyl acetate. The upper layer was separated, washed with saturated saline to neutrality, and dried over anhydrous sodium sulfate. The solvent was removed. Distillation under reduced pressure gave diethyl 2,2′-biphenyldicarboxylate as a colorless liquid, and the yield was 90%.

Workup

  1. temperatureThen the reaction mixture was heated
  2. temperaturerefluxing
  3. customwas removed
  4. customseparated
  5. extractionextracted with ethyl acetate
  6. customThe upper layer was separated
  7. washwashed with saturated saline to neutrality
  8. dry with materialdried over anhydrous sodium sulfate
  9. customThe solvent was removed
  10. distillationDistillation under reduced pressure

Sources & evidence

ORD record
ord-8e657e9a56ee4cfabb358574cb2a8f22
Source dataset
uspto-grants-2008_06
Patent number
US07388061B2

Reaction notes

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