Ethyl 3-(trifluoromethyl)non-2-enoate → HCID 54107361, compound

HRID 893539Notes

Reaction equation

HRID 893539 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])=[CH:4][C:5]([O:7]CC)=[O:6].[H][H]>CO.[Pd]>[F:1][C:2]([F:16])([F:17])[C:3]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])=[CH:4][C:5]([OH:7])=[O:6]

Participants

5

Reactant 2

HCID 53647231Ethyl 3-(trifluoromethyl)non-2-enoateHCID 178418361HCID 178418361, compound

Product 1

HCID 54107361HCID 54107361, compoundYield 112.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

13.78 g of ethyl 3-trifluoromethyl-2-nonenoate was dissolved in 138 ml of methanol, and 1.38 g of 5%-palladium/activated carbon was added thereto, followed by stirring for 4 hours at room temperature and normal pressure in a hydrogen atmosphere in a catalytic hydrogenation apparatus. After the reaction, the 5%-palladium/activated carbon was filtered out, and the remaining methanol solution was mixed with 24 ml, of water and 20 g of potassium hydroxide, followed by 2 hours of heat refluxing, distilling-off of methanol under a reduced pressure, acidification with addition of 6N-hydrochloric acid, and extraction with methylene chloride. The resultant methylene chloride solution was dried on sodium sulfate, followed by distilling-off of the solvent and purification by distillation (b.p.: 118.5°-119.7° C./20 mmHg), whereby 13.78 g of 3-trifluoromethylnonenoic acid was obtained. (Yield: 51.5%).

Workup

  1. customAfter the reaction
  2. filtrationthe 5%-palladium/activated carbon was filtered out
  3. additionthe remaining methanol solution was mixed with 24 ml, of water and 20 g of potassium hydroxide
  4. waitfollowed by 2 hours
  5. temperatureof heat
  6. temperaturerefluxing, distilling-off of methanol under a reduced pressure, acidification with addition of 6N-hydrochloric acid, and extraction with methylene chloride
  7. dry with materialThe resultant methylene chloride solution was dried on sodium sulfate
  8. distillationfollowed by distilling-off of the solvent and purification by distillation (b.p.: 118.5°-119.7° C./20 mmHg)

Sources & evidence

ORD record
ord-7e42de5ea2f7456ea685722f668877aa
Source dataset
uspto-grants-1992_06
Patent number
US05126071

Reaction notes

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