Hydrochloric Acid → 2-(5,5-ethylenedioxy-5H-dibenzo[a,d]cyclohepten-2-yl)propionic acid

HRID 972981Notes

Reaction equation

HRID 972981 reaction equation
[CH2:1]1[CH2:23][O:22][C:3]2([C:9]3[CH:10]=[CH:11][C:12]([CH:14]([CH3:17])[C:15]#N)=[CH:13][C:8]=3[CH:7]=[CH:6][C:5]3[CH:18]=[CH:19][CH:20]=[CH:21][C:4]2=3)[O:2]1.[OH-:24].[K+].Cl.[OH2:27]>>[CH2:1]1[CH2:23][O:22][C:3]2([C:9]3[CH:10]=[CH:11][C:12]([CH:14]([CH3:17])[C:15]([OH:27])=[O:24])=[CH:13][C:8]=3[CH:7]=[CH:6][C:5]3[CH:18]=[CH:19][CH:20]=[CH:21][C:4]2=3)[O:2]1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14797Potassium HydroxideHCID 214031012-(5,5-ethylenedioxy-5H-dibenzo[a,d]cyclohepten-2-yl)propionitrile

Product 1

HCID 214030932-(5,5-ethylenedioxy-5H-dibenzo[a,d]cyclohepten-2-yl)propionic acidYield 75%

Procedure

0.7 Gm. of 2-(5,5-ethylenedioxy-5H-dibenzo[a,d]cyclohepten-2-yl)propionitrile is refluxed for 9 hours in 40 ml. of water containing 1.1 gm. of potassium hydroxide. The solution is cooled and neutralized with dilute hydrochloric acid, and extracted with ether. The ether extract is washed, dried and evaporated to afford a 75% yield of 2-(5,5-ethylenedioxy-5H-dibenzo[a,d]cyclohepten-2-yl)propionic acid. Use of 2-(5,5-ethylenedioxy)-5H-dibenzo[a,d]cyclohepten-2-yl)acetonitrile gives a similar yield of 2-(5,5-ethylenedioxy-5H-dibenzo[a,d]cyclohepten-2-yl)acetic acid.

Workup

  1. temperatureThe solution is cooled
  2. extractionextracted with ether
  3. extractionThe ether extract
  4. washis washed
  5. customdried
  6. customevaporated

Sources & evidence

ORD record
ord-d3e89b28125443ea8d63e3812b3304d7
Source dataset
uspto-grants-1977_10
Patent number
US04054579

Reaction notes

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