Hydrochloric Acid → HCID 86653387, compound

HRID 1192774Notes

Reaction equation

HRID 1192774 reaction equation
[C:1]([O:24]CC)(=[O:23])/[CH:2]=[CH:3]\[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=[CH:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22].[OH-].[Na+].O.Cl>CO>[C:1]([OH:24])(=[O:23])/[CH:2]=[CH:3]\[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=[CH:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 86653388HCID 86653388, compound

Product 1

HCID 86653387HCID 86653387, compoundYield 91.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of ethyl cis-docosahexaenoate (5 g, 14.0 mmol) in methanol (100 mL) was added an aqueous solution of NaOH (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 DCM (3×50 mL) and the combined layer was washed with water, brine and dried over sodium sulfate. The solution was filtered and the solvent evaporated to give the acid (4.2 g, 91%) as an oil; LCMS (ESI, negative ion mode): m/z 327 (M-H)−.

Workup

  1. additionThe reaction mixture was poured into ice
  2. extractionThe solution was extracted with DCM (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. customthe solvent evaporated

Sources & evidence

ORD record
ord-420261405f3f43e38a3e3ccc18f4363e
Source dataset
uspto-grants-2014_03
Patent number
US08680143B2

Reaction notes

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