Ethylene Glycol → 6,7-dihydro-5H-dibenzo[a,c]cycloheptene-4-carboxylic acid

HRID 2164832Notes

Reaction equation

HRID 2164832 reaction equation
[CH:1]1[C:6]2[C:7]3[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=3[CH2:9][CH2:10][CH2:11][C:5]=2C(C#N)=[CH:3][CH:2]=1.[OH-:18].[K+].[CH2:20]([OH:23])[CH2:21]O>O>[CH:1]1[C:6]2[C:7]3[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=3[CH2:9][CH2:10][CH2:11][C:5]=2[C:21]([C:20]([OH:23])=[O:18])=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 14797Potassium HydroxideHCID 132813406,7-dihydro-5H-dibenzo[a,c]cyclohepten-4-carbonitrile

Product 1

HCID 132813416,7-dihydro-5H-dibenzo[a,c]cycloheptene-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Under a dry nitrogen atmosphere a solution of 6,7-dihydro-5H-dibenzo[a,c]cycloheptene-4-carbonitrile (2.95 grams, 0.0134 mole), potassium hydroxide (4 grams, 0.085 mole), ethylene glycol (40 ml) and water (3 ml) was heated at reflux for approximately 24 hours. The mixture was cooled, diluted with water, and the solution was washed with diethyl ether. The aqueous solution was acidified and extracted with diethyl ether. The extract was dried over anhydrous magnesium sulfate and filtered. The filtrate was evaporated to give a white solid. The solid was combined with similar material prepared in a separate experiment, and the combined solids were recrystallized from n-hexane to give 6,7-dihydro-5H-dibenzo[a,c]cycloheptene-4-carboxylic acid (mp 137°-139°) as nearly white crystals.

Workup

  1. temperatureat reflux for approximately 24 hours
  2. temperatureThe mixture was cooled
  3. washthe solution was washed with diethyl ether
  4. extractionextracted with diethyl ether
  5. dry with materialThe extract was dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customThe filtrate was evaporated
  8. customto give a white solid
  9. customprepared in a separate experiment
  10. customthe combined solids were recrystallized from n-hexane

Sources & evidence

ORD record
ord-722837a1aad9402d8b9878980dcd432e
Source dataset
uspto-grants-1985_03
Patent number
US04507317

Reaction notes

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