Hydrochloric Acid → HCID 54056444, compound

HRID 542150Notes

Reaction equation

HRID 542150 reaction equation
[OH-].[K+].C(O)(C)C.[CH3:7][C:8]([CH2:15][CH:16](S(C1C=CC(C)=CC=1)(=O)=O)[CH:17]=[C:18]([CH3:35])[CH2:19][CH2:20][CH:21]=[C:22]([CH3:34])[CH2:23][CH2:24][CH:25]=[C:26]([CH3:33])[CH2:27][CH2:28][CH:29]=[C:30]([CH3:32])[CH3:31])=[CH:9][C:10]([O:12]CC)=[O:11].Cl>CCCCCC>[CH3:7][C:8]([CH:15]=[CH:16][CH:17]=[C:18]([CH3:35])[CH2:19][CH2:20][CH:21]=[C:22]([CH3:34])[CH2:23][CH2:24][CH:25]=[C:26]([CH3:33])[CH2:27][CH2:28][CH:29]=[C:30]([CH3:32])[CH3:31])=[CH:9][C:10]([OH:12])=[O:11]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3776IsopropanolHCID 14797Potassium HydroxideHCID 54094541HCID 54094541, compound

Product 1

HCID 54056444HCID 54056444, compound

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

To 4.1 g. of potassium hydroxide in 50 ml. of isopropyl alcohol was added 12 g. of the above-obtained ethyl 3,7,11,15,19-pentamethyl-5-p-tolylsulfonyl-2,6,10,14,18-eicosapentaenoate, and the mixture was stirred at 50° C. for 3 hours. The reaction liquid was poured into ice-water, made acidic by addition of hydrochloric acid, and extracted with 100 ml. of diethyl ether. The extract was washed with water, dried over magnesium sulfate and evaporated to remove the solvent. There was obtained 8.5 g. of an oil. The so obtained oil was dissolved in 40 ml. of n-hexane and chilled to -20° C. to crystallize. There was obtained 2.3 g. of the desired product as white crystals.

Workup

  1. customThe reaction liquid
  2. extractionextracted with 100 ml
  3. washThe extract was washed with water
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customto remove the solvent
  7. customThere was obtained 8.5 g
  8. dissolutionThe so obtained oil was dissolved in 40 ml
  9. customto crystallize
  10. customThere was obtained 2.3 g

Sources & evidence

ORD record
ord-3864362e5d324a7f9033c2018aff164a
Source dataset
uspto-grants-1987_04
Patent number
US04655973

Reaction notes

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