Hydrochloric Acid → ACMC-20apjz

HRID 918111Notes

Reaction equation

HRID 918111 reaction equation
C[O:2][C:3]1[CH2:7][CH:6]([OH:8])[C:5](=O)[C:4]=1[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([OH:18])=[O:17].[H-].[Na+].[H-].[Al+3].[Li+].[H-].[H-].[H-].Cl>CN(C)P(N(C)C)(N(C)C)=O.C(Cl)(Cl)Cl.O>[OH:8][CH:6]1[CH2:7][C:3](=[O:2])[C:4]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([OH:18])=[O:17])=[CH:5]1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 21226445Aluminium lithium hydrideHCID 215229427-(4-Hydroxy-2-methoxy-5-oxocyclopent-1-en-1-yl)heptanoic acid

Product 1

HCID 3690897ACMC-20apjz

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6212ChloroformSolventHCID 12679HexamethylphosphoramideSolvent

Procedure

A solution of 0.500 part of 2-methoxy-4-hydroxy-5-oxocyclopent-1-eneheptanoic acid dissolved in 25 parts by volume of hexamethyl phosphoramide is treated with 0.094 part of sodium hydride and stirred for 11/2 hours. Then 8.5 parts by volume of lithium aluminum hydride is added and the reaction mixture is stirred at room temperature for 1/2 hour and then heated at 70°-75° for 13/4 hours. The solution is acidified with hydrochloric acid and allowed to stand at room temperature for about 16 hours. Water and chloroform then are added to form 2 layers which are separated. The organic layer is extracted with 5% aqueous sodium carbonate. The sodium carbonate extracts are washed with chloroform and then acidified with hydrochloric acid. The acidified extracts are themselves extracted with ethyl acetate and washed with water, dried over anhydrous sodium sulfate and stripped of solvent. In that manner there is afforded 3-hydroxy-5-oxocyclopent-1-eneheptanoic acid.

Workup

  1. stirringthe reaction mixture is stirred at room temperature for 1/2 hour
  2. temperatureheated at 70°-75° for 13/4 hours
  3. waitto stand at room temperature for about 16 hours
  4. customare separated
  5. extractionThe organic layer is extracted with 5% aqueous sodium carbonate
  6. washThe sodium carbonate extracts are washed with chloroform
  7. extractionextracted with ethyl acetate
  8. washwashed with water
  9. dry with materialdried over anhydrous sodium sulfate

Sources & evidence

ORD record
ord-fe89430d10334b00bb409eccb9fadf0e
Source dataset
uspto-grants-1976_07
Patent number
US03969391

Reaction notes

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