Hydrochloric Acid → 12-Methoxyoctadec-9-enoic acid

HRID 1291691Notes

Reaction equation

HRID 1291691 reaction equation
[CH3:1][O:2][CH:3]([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH2:4][CH:5]=[CH:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([O:16]CC)=[O:15].C(O)C.[OH-].[K+].Cl>CCCCCC>[CH3:1][O:2][CH:3]([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH2:4][CH:5]=[CH:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([OH:16])=[O:15]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14797Potassium HydroxideHCID 54363898HCID 54363898, compound

Product 1

HCID 5440421812-Methoxyoctadec-9-enoic acidYield 93.3%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
50 °C

Procedure

Next, to a 1-l flask equipped with a stirrer, 68.1 g (0.2 mol) of ethyl 12-methoxy-9-octadecenoate, 600 ml of ethanol and 45 g of a 50% aqueous solution of potassium hydroxide were charged, followed by stirring at 50° C. for 4 hours. To the reaction mixture so obtained, hexane was added, followed by neutralization with 3N hydrochloric acid and then washing with saturated saline. After concentration under reduced pressure, the residue was purified by chromatography on a silica gel column, whereby 58.3 g of the title compound (8-d) were obtained (yield: 93%).

Workup

  1. customNext, to a 1-l flask equipped with a stirrer
  2. customTo the reaction mixture so obtained
  3. washwashing with saturated saline
  4. concentrationAfter concentration under reduced pressure
  5. customthe residue was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-9b254e8102c54152bdd56b97bedb6342
Source dataset
uspto-grants-1998_05
Patent number
US05753707

Reaction notes

Loading…