Hydrochloric Acid → 11-(3,5-Bis(trifluoromethyl) phenoxy)dodecanoic acid

HRID 1363871Notes

Reaction equation

HRID 1363871 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:4]=[C:5]([OH:13])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.Br[CH:17]([CH3:30])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][C:27]([OH:29])=[O:28].Cl>[OH-].[Na+]>[F:1][C:2]([F:14])([F:15])[C:3]1[CH:4]=[C:5]([CH:6]=[C:7]([C:9]([F:11])([F:10])[F:12])[CH:8]=1)[O:13][CH:17]([CH3:30])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][C:27]([OH:29])=[O:28]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 676803,5-Bis(trifluoromethyl)phenolHCID 531294511-Bromododecanoic acid

Product 1

HCID 8662056111-(3,5-Bis(trifluoromethyl) phenoxy)dodecanoic acidYield 255.2%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

3,5-Bis(trifluoromethyl) phenol (20.6 g) was dissolved in 1N sodium hydroxide (270 mL). The solution was refluxed under heating for 10 hours. After addition of 11-bromododecanoic acid (4.7 g), the solution was kept refluxed under heating, and then left to be cooled. The reaction solution was added with 1N aqueous hydrochloric acid and extracted with ethyl acetate. The resulting organic layer was dried over anhydrous magnesium sulfate, and the solvent was removed. The resulting crystals was washed with hexane and purified by silica gel column chromatography to obtain 11-(3,5-bis(trifluoromethyl) phenoxy)dodecanoic acid (18.4 g, 50%).

Workup

  1. temperatureThe solution was refluxed
  2. temperatureunder heating for 10 hours
  3. temperaturethe solution was kept refluxed
  4. temperatureunder heating
  5. waitleft
  6. temperatureto be cooled
  7. extractionextracted with ethyl acetate
  8. dry with materialThe resulting organic layer was dried over anhydrous magnesium sulfate
  9. customthe solvent was removed
  10. washThe resulting crystals was washed with hexane
  11. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-4a80fb6012b64186bf53eabfc2d6533a
Source dataset
uspto-grants-2011_02
Patent number
US07887835B2

Reaction notes

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