Hydrochloric Acid → HCID 25010325, compound

HRID 1925669Notes

Reaction equation

HRID 1925669 reaction equation
[CH3:1]/[C:2](/[CH2:9][CH2:10][CH2:11]/[CH:12]=[CH:13]\[CH2:14]/[CH:15]=[CH:16]\[CH2:17]/[CH:18]=[CH:19]\[CH2:20]/[CH:21]=[CH:22]\[CH2:23]/[CH:24]=[CH:25]\[CH2:26][CH3:27])=[CH:3]\[C:4]([O:6]CC)=[O:5].[Li+].[OH-].Cl>CO.O>[CH3:1]/[C:2](/[CH2:9][CH2:10][CH2:11]/[CH:12]=[CH:13]\[CH2:14]/[CH:15]=[CH:16]\[CH2:17]/[CH:18]=[CH:19]\[CH2:20]/[CH:21]=[CH:22]\[CH2:23]/[CH:24]=[CH:25]\[CH2:26][CH3:27])=[CH:3]\[C:4]([OH:6])=[O:5]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 25010497HCID 25010497, compound

Product 1

HCID 25010325HCID 25010325, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

Ethyl (2E,7Z,10Z,13Z,16Z,19Z)-3-methyl-docosa-2,7,10,13,16,19-hexaenoate (3) was dissolved in methanol (9 ml) and added LiOH (220 mg, 4.89 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 4. 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), 1.55 (m, 2H), 2.0-2.2 (m, 6H), 2.15 (d, J 1.3, 3H, CH3), 2.7-2.9 (m, 8H), 5.2-5.5 (m, 10H), 5.68 (br s, 1H); δc(75 MHz) 14.24, 19.04, 20.53, 25.51, 25.60, 25.62, 25.64, 26.67, 27.28, 40.67, 115.24, 126.99, 127.84, 128.05, 128.11, 128.19, 128.22, 128.53, 128.57, 129.23, 132.00, 163.05, 172.31.

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-7b6f513a25ec45c4a52541d81af869e4
Source dataset
uspto-grants-2012_05
Patent number
US08178708B2

Reaction notes

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