Hydrochloric Acid → HCID 12387346, compound

HRID 358808Notes

Reaction equation

HRID 358808 reaction equation
[CH2:1]([C:8]1[CH:13]=[CH:12][C:11](C2OCCN(C(=S)C)C2)=[CH:10][CH:9]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].C(O)COCCO[CH2:29][CH2:30][OH:31].[OH-:33].[K+].Cl>O>[CH2:1]([C:8]1[CH:9]=[CH:10][C:11]([CH2:29][C:30]([OH:31])=[O:33])=[CH:12][CH:13]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8172Triethylene GlycolHCID 14797Potassium HydroxideHCID 131716805HCID 131716805, compound

Product 1

HCID 12387346HCID 12387346, compoundYield 18%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 56.1 g of the 4-[2-(4-heptylphenyl)-1-thioxoethylmorpholine thus obtained, were added 300 ml of triethylene glycol, 50 ml of water and 37.3 g of potassium hydroxide. The resulting mixture was heated under reflux for six hours and then allowed to cool to room temperature. Then 10% hydrochloric acid was added thereto by portions until the pH value of the solution became slightly acidic. The reaction product was extracted with 300 ml of ethyl acetate and the organic layer was washed with water until the aqueous layer became neutral. Then the organic layer was separated and dried over anhydrous sodium sulfate. After distilling off the solvent, the residue was recrystallized from hexane. Thus 28.0 g of p-heptylphenylacetic acid was obtained. Yield: 18%.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureunder reflux for six hours
  3. extractionThe reaction product was extracted with 300 ml of ethyl acetate
  4. washthe organic layer was washed with water until the aqueous layer
  5. customThen the organic layer was separated
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationAfter distilling off the solvent
  8. customthe residue was recrystallized from hexane

Sources & evidence

ORD record
ord-2b8d015b81f3484a952888db43b87865
Source dataset
uspto-grants-1991_03
Patent number
US04997942

Reaction notes

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