Ethylene Glycol → HCID 54259475, compound

HRID 1758263Notes

Reaction equation

HRID 1758263 reaction equation
[CH:1]([CH:4]([C:7]1[CH:15]=[CH:14][C:10]2[CH:11]=[CH:12][O:13][C:9]=2[CH:8]=1)[C:5]#N)([CH3:3])[CH3:2].[OH-:16].[K+].C(O)C[OH:20]>O>[CH:1]([CH:4]([C:7]1[CH:15]=[CH:14][C:10]2[CH:11]=[CH:12][O:13][C:9]=2[CH:8]=1)[C:5]([OH:20])=[O:16])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 14797Potassium HydroxideHCID 54066355HCID 54066355, compound

Product 1

HCID 54259475HCID 54259475, compoundYield 50.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
140 °C

Procedure

A mixture of α-isopropylbenzofuran-6-acetonitrile (1.62 g, 0.008 mol), potassium hydroxide (2.29 g, 0.039 mol), ethane-1,2-diol (28 cm3) and water (2.3 cm3) was refluxed at 140° C. for 18 hr. The cooled mixture was poured into water and extracted with diethyl ether. The aqueous solution was acidified with hydrochloric acid and the mixture was extracted with diethyl ether. The ether extract was washed with water, dried (Na2SO4), filtered and the solvent was removed to give α-isopropylbenzofuran-6-acetic acid (0.90 g, 0.0041 mol, 50.8%). Recrystallised from petroleum ether (b.p. 60°-80° C.) m.p. 99°-100° C. (Found: C, 71.52; H, 6.65; C13H14O3 requires C, 71.54; H, 6.47%), t.l.c./silica/ethyl acetate RF 0.40.

Workup

  1. extractionextracted with diethyl ether
  2. extractionthe mixture was extracted with diethyl ether
  3. extractionThe ether extract
  4. washwas washed with water
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customthe solvent was removed

Sources & evidence

ORD record
ord-4c00e3c704d840b78106dd02db71ab06
Source dataset
uspto-grants-1983_02
Patent number
US04372970

Reaction notes

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