HCID 10893325, compound → 10-Hydroxy-9-methoxyoctadecanoic acid

HRID 2279686Notes

Reaction equation

HRID 2279686 reaction equation
[OH:1][CH:2]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH:3]([O:15][CH3:16])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]([O:13]C)=[O:12]>[OH-].[Na+].CO>[OH:1][CH:2]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH:3]([O:15][CH3:16])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]([OH:13])=[O:12]

Participants

3

Reactant 1

HCID 10893325HCID 10893325, compound

Product 1

HCID 1384764910-Hydroxy-9-methoxyoctadecanoic acid

Reagents, catalysts & solvents 1

HCID 23721981Sodium hydroxide methanolSolvent

Procedure

The methyl 10-hydroxy-9-methoxyoctadecanoate (3) (4.0 g; 0.012 mol) was dissolved in 1N methanol sodium hydroxide solution (100 mL) (Aldrich) and heated under reflux for 12 h. The methanol was removed from the reaction mixture and the crude product was dissolved in 100 mL water. The aqueous solution was neutralised with hydrochloric acid (Aldrich) and the product extracted with 3×50 mL dichloromethane (J. T. Baker). The dichloromethane solution was washed with 3×50 mL water and dried over anhydrous sodium sulfate (J. T. Baker). The dichloromethane solution was filtered and the solvent was removed to obtain the intermediate compound 4.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 12 h
  3. customThe methanol was removed from the reaction mixture
  4. dissolutionthe crude product was dissolved in 100 mL water
  5. extractionthe product extracted with 3×50 mL dichloromethane (J. T. Baker)
  6. washThe dichloromethane solution was washed with 3×50 mL water
  7. dry with materialdried over anhydrous sodium sulfate (J. T. Baker)
  8. filtrationThe dichloromethane solution was filtered
  9. customthe solvent was removed

Sources & evidence

ORD record
ord-001faf2151134d449a741a7f2a4e2688
Source dataset
uspto-grants-2015_09
Patent number
US09133305B2

Reaction notes

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