Hydrochloric Acid → HCID 21641527, compound

HRID 355321Notes

Reaction equation

HRID 355321 reaction equation
[OH-:1].[K+].CC(C[C:16]1[CH:25]=[CH:24][C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=1)(C(OCC)=O)C(OCC)=O.Cl.[OH2:27]>C(O)C.C(OCC)(=O)C>[CH3:17][CH:18]([CH2:23][C:19]1[C:18]2[C:23](=[CH:24][CH:25]=[CH:16][CH:17]=2)[CH:22]=[CH:21][CH:20]=1)[C:19]([OH:27])=[O:1]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962Water2×HCID 14797Potassium HydroxideHCID 21805819HCID 21805819, compound

Product 1

HCID 21641527HCID 21641527, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
175 °C

Procedure

A solution of 23.7 g (422 mmol) of potassium hydroxide in 50 ml of water was added to 33.2 g (105 mmol) of the compound 1 in 70 ml of ethanol, and the mixture was heated under reflux for 4 hours. After the solvent had been stripped off, the solid residue was taken up in ethyl acetate, water was added and the pH was brought to 1 with hydrochloric acid. The aqueous phase was extracted several times with ethyl acetate. After drying over magnesium sulfate, the combined organic phases were evaporated completely. The residue was stirred with hexane for crystallization. For decarboxylation, the beige-colored solid was heated at 175° C. until the evolution of gas had ended. 21 g (94%) of the product 2 were obtained as a beige-colored solid.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 4 hours
  3. extractionThe aqueous phase was extracted several times with ethyl acetate
  4. dry with materialAfter drying over magnesium sulfate
  5. customthe combined organic phases were evaporated completely

Sources & evidence

ORD record
ord-53468a0e7a0647719b6c3d2ca2ec3f48
Source dataset
uspto-grants-1998_11
Patent number
US05830821

Reaction notes

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