Hydrochloric Acid → HCID 57897420, compound

HRID 1696608Notes

Reaction equation

HRID 1696608 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([C:9]([F:12])([F:11])[F:10])[CH:3]=1.[OH-:13].[Na+].Cl>C(Cl)(Cl)Cl.CC(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:4]([CH3:9])([CH3:3])[C:5]([OH:8])=[O:13])=[C:4]([C:9]([F:10])([F:11])[F:12])[CH:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 129181514-Chloro-2-(trifluoromethyl)phenol

Product 1

HCID 57897420HCID 57897420, compoundYield 37%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6212ChloroformSolvent

Procedure

A three-neck round bottom flask affixed with an overhead stirrer was charged with 4-chloro-2-(trifluoromethyl)phenol (prepared according methods described in U.S. Pat. No. 4,262,152), (5.0 g, 127 mmol, 1.0 eq) and dissolved in chloroform (3.3 mL) and acetone (8.4 mL). NaOH pellets (4.2 g, 104 mmol, 3.75 eq) were added in 2 portions and the mixture was stirred vigorously for 40 min. The resulting slurry was acidified to pH 2 with 3N HCl and extracted with EtOAc. The organic extracts were treated with satd. aq. sodium bicarbonate, and the basic layer was acidified to pH 4 with conc. HCl and extracted with EtOAc. The organic layer was washed with brine, dried over sodium sulfate and concentrated to afford 2.7 g (37%) of 2-(4-chloro-2-(trifluoromethyl)phenoxy)-2-methylpropanoic acid as a light brown crystalline solid. 1H NMR (400 MHz, CDCl3): δ 7.57 (d, J=2.6 Hz, 1H), 7.40 (dd, J=8.9, 2.6 Hz, 1H), 6.91 (d, J=8.9 Hz, 1H), 1.67 (s, 6H). LCMS (0-99% MeCN/water, 5 min, negative ion), Tret=2.99 min, [M−H]−=281.3 observed.

Workup

  1. customA three-neck round bottom flask affixed with an overhead stirrer
  2. customprepared
  3. additionwere added in 2 portions
  4. extractionextracted with EtOAc
  5. additionThe organic extracts were treated with satd
  6. extractionextracted with EtOAc
  7. washThe organic layer was washed with brine
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-7b8696bf6f20499f8f690a30785e075f
Source dataset
uspto-grants-2012_04
Patent number
US08163771B2

Reaction notes

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