Hydrochloric Acid → HCID 25010493, compound

HRID 1925671Notes

Reaction equation

HRID 1925671 reaction equation
[CH3:1]/[C:2](=[CH:8]\[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]/[CH:16]=[CH:17]\[CH2:18]/[CH:19]=[CH:20]\[CH2:21]/[CH:22]=[CH:23]\[CH2:24][CH3:25])/[C:3]([O:5]CC)=[O:4].[Li+].[OH-].Cl>CO.O>[CH3:1]/[C:2](=[CH:8]\[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]/[CH:16]=[CH:17]\[CH2:18]/[CH:19]=[CH:20]\[CH2:21]/[CH:22]=[CH:23]\[CH2:24][CH3:25])/[C:3]([OH:5])=[O:4]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 25010496HCID 25010496, compound

Product 1

HCID 25010493HCID 25010493, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

Ethyl (2E,11Z,14Z,17Z)-2-methyl-eicosa-2,11,14,17-tetraenoate (6) (160 mg, 0.46 mmol) was dissolved in methanol (3 ml) and added LiOH (193 mg, 4.6 mmol) in water (3 ml) and the mixture was heated at 50° C. for 2 hrs. The mixture was cooled, and diluted hydrochloric acid was added to pH 2. Extraction with diethylether, drying (MgSO4) and evaporation of solvents under reduced pressure afforded the acid 7. The acid was purified by flash chromatography on silica gel (8:2 hexane-EtOAc); δH(300 MHz) 0.95 (t, J 7.5, 3H, CH3), 1.2-1.5 (m, 10H), 1.81 (s, 3H, CH3), 2.0-2.2 (m, 6H), 2.79 (t, J 5.8, 4H), 5.2-5.4 (m, 6H), 6.90 (dt, J 7.5, J 1.3, 1H); δc(75 MHz) 11.93, 14.25, 20.53, 25.51, 25.60, 27.19, 28.40, 28.87, 29.16, 29.31, 29.58, 126.94, 127.10, 127.71, 128.24, 128.25, 130.25, 131.93, 145.41, 173.76.

Workup

  1. temperatureThe mixture was cooled
  2. extractionExtraction with diethylether
  3. customdrying
  4. custom(MgSO4) and evaporation of solvents under reduced pressure

Sources & evidence

ORD record
ord-f0b66733a83243e9ac726b140519bba4
Source dataset
uspto-grants-2012_05
Patent number
US08178708B2

Reaction notes

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