Hydrochloric Acid → HCID 86653383, compound

HRID 1192771Notes

Reaction equation

HRID 1192771 reaction equation
[C:1]([O:22]CC)(=[O:21])/[CH:2]=[CH:3]\[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=[CH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20].[OH-].[Na+].O.Cl>CO>[C:1]([OH:22])(=[O:21])/[CH:2]=[CH:3]\[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=[CH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 86653384HCID 86653384, compound

Product 1

HCID 86653383HCID 86653383, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of ethyl cis-eicosapentaenoate (5 g, 15.15 mmol) in methanol (100 mL) was added an aqueous solution of sodium hydroxide (6 g, 150 mmol, in 20 mL of water) at rt and stirred for 1.5 h. The reaction mixture was poured into ice cooled water and acidified with dil. HCl. The solution was extracted with dichloromethane (3×50 mL) and the combined layer was washed with water, brine and dried over sodium sulfate. The solution was filtered and evaporated the solvent to give the acid (4.4 g, 96%) as an oil; LCMS (ESI, negative ion mode): m/z 301 (M-H)−.

Workup

  1. additionThe reaction mixture was poured into ice
  2. extractionThe solution was extracted with dichloromethane (3×50 mL)
  3. washthe combined layer was washed with water, brine
  4. dry with materialdried over sodium sulfate
  5. filtrationThe solution was filtered
  6. customevaporated the solvent

Sources & evidence

ORD record
ord-bd39403ef11842a58339ec8f4a9d45f0
Source dataset
uspto-grants-2014_03
Patent number
US08680143B2

Reaction notes

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