Water → 2,4,5-Trifluoro-3-isopropyloxybenzoic acid

HRID 369315Notes

Reaction equation

HRID 369315 reaction equation
[F:1][C:2]1[C:10]([OH:11])=[C:9]([F:12])[C:8]([F:13])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH:14](I)([CH3:16])[CH3:15].O.[OH-].[Na+]>C(O)C>[F:1][C:2]1[C:10]([O:11][CH:14]([CH3:16])[CH3:15])=[C:9]([F:12])[C:8]([F:13])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

6

Reactant 4

HCID 962WaterHCID 6362Isopropyl iodideHCID 14798Sodium HydroxideHCID 27342702,4,5-Trifluoro-3-hydroxybenzoic Acid

Product 1

HCID 232847882,4,5-Trifluoro-3-isopropyloxybenzoic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2,4,5-Trifluoro-3-hydroxybenzoic acid (4.0 g) was added together with isopropyl iodide (4.7 g) to a mixed liquid of distilled water (10 ml) and ethanol (20 ml), in which sodium hydroxide (1.83 g) had been dissolved. The mixture was stirred and heated under reflux for 23 hours. The reaction mixture was concentrated under reduced pressure. The resultant residue was acidified with concentrated hydrochloric acid, and water (25 ml) was added to conduct extraction twice with chloroform (25 ml). A collected chloroform layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The resultant residue was subjected to column chromatography (silica gel: 75 g, eluent; chloroform: methanol:acetic acid=500:20:1) to obtain 2,4,5-trifluoro-3-isopropyloxybenzoic acid as a solid residue.

Workup

  1. dissolutionhad been dissolved
  2. temperatureheated
  3. temperatureunder reflux for 23 hours
  4. concentrationThe reaction mixture was concentrated under reduced pressure
  5. additionwas added
  6. extractionextraction twice with chloroform (25 ml)
  7. dry with materialA collected chloroform layer was dried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7dfd9c286d1f453eadfc17e9cb78a4a5
Source dataset
uspto-grants-2000_10
Patent number
US06136823

Reaction notes

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