Ethylene Glycol → 3,3-Diphenylacrylic acid

HRID 469263

Reaction equation

HRID 469263 reaction equation
[C:1]1([C:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=CC#N)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-:17].[Na+].Cl.[CH2:20]([OH:23])[CH2:21]O>O>[C:1]1([C:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:21][C:20]([OH:23])=[O:17])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 2743523,3-Diphenylacrylonitrile

Product 1

HCID 118263,3-Diphenylacrylic acidYield 81%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of 3,3-diphenylacrylonitrile (5.76 g, 28.1 mmol) and sodium hydroxide (11.2 g) in ethylene glycol (180 mL) and water (1 mL) were refluxed for 3 days. The reaction mixture was diluted with water (100 mL), acidified with 5N HCl to pH˜1, and extracted with ethyl acetate. The organic extract was washed with water, dried over sodium sulfate, and concentrated in vacuo. The crude material was purified by flash column chromatography ethyl acetate/hexanes to give 3,3-diphenylacrylic acid (5.1 g, 81%) as a white powder.

Workup

  1. temperaturewere refluxed for 3 days
  2. extractionextracted with ethyl acetate
  3. extractionThe organic extract
  4. washwas washed with water
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe crude material was purified by flash column chromatography ethyl acetate/hexanes

Sources & evidence

ORD record
ord-4013f70533ea4b51b777c2b2ef3ec886
Source dataset
uspto-grants-2014_01
Patent number
US08629149B2

Linked notes

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