Ethylene Glycol → HCID 14229717, compound

HRID 1761913Notes

Reaction equation

HRID 1761913 reaction equation
[CH3:1][C:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[C:10]([C:11]#N)[C:5]=2[O:4][C:3]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[OH-:19].[Na+].C(O)CO.Cl.[OH2:26]>>[CH3:1][C:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[C:10]([C:11]([OH:26])=[O:19])[C:5]=2[O:4][C:3]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 5

HCID 174Ethylene GlycolHCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 14229702HCID 14229702, compound

Product 1

HCID 14229717HCID 14229717, compound

Procedure

A mixture of 364 mg of 3-methyl-2-phenylbenzofuran-7-nitrile, 3 g of an aqueous 30% sodium hydroxide solution and 8 ml of ethylene glycol is refluxed for 2 hours. After cooling, the reaction mixture is poured into water, acidified with 10% hydrochloric acid and then extracted with ethyl acetate. The extract is washed with a saturated sodium chloride solution, dried and evaporated to remove solvent. The residue is recrystallized from tetrahydrofuran-n-hexane to give 257 mg of 3-methyl-2-phenylbenzofuran-7-carboxylic acid as colorless prisms.

Workup

  1. temperatureis refluxed for 2 hours
  2. temperatureAfter cooling
  3. extractionextracted with ethyl acetate
  4. washThe extract is washed with a saturated sodium chloride solution
  5. customdried
  6. customevaporated
  7. customto remove solvent
  8. customThe residue is recrystallized from tetrahydrofuran-n-hexane

Sources & evidence

ORD record
ord-ef38972e7dc34559bf8d2035e287761c
Source dataset
uspto-grants-1989_05
Patent number
US04829067

Reaction notes

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