Acetic Acid → 4-Ethoxy-2-(trifluoromethyl)phenol

HRID 1789632Notes

Reaction equation

HRID 1789632 reaction equation
C(O)(=O)C.[CH2:5]([O:7][C:8]1[CH:13]=[CH:12][C:11]([O:14]B(O)O)=[C:10]([C:18]([F:21])([F:20])[F:19])[CH:9]=1)[CH3:6].O.OO.S([O-])(O)=O.[Na+]>C1COCC1>[CH2:5]([O:7][C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[C:10]([C:18]([F:19])([F:20])[F:21])[CH:9]=1)[CH3:6]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 449047Hydrogen peroxide waterHCID 220350064-ethoxy-2-trifluoromethylphenylboric AcidHCID 23665763Sodium Bisulfite

Product 1

HCID 220349974-Ethoxy-2-(trifluoromethyl)phenolYield 97.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Acetic acid (21.3 g) was added to a mixture of THF (200 mL) and Compound (d) (8.28 g) at room temperature, and the mixture was stirred at 0° C. under a nitrogen atmosphere. After adding 30% hydrogen peroxide water (40.1 g) dropwise, the resulting reaction mixture was carefully heated and stirred at 50° C. for 4 hours. Saturated aqueous sodium hydrogen sulfite (200 mL) was then slowly added dropwise at 0° C., and the reaction mixture was extracted three times with ether. The organic layers were combined, washed with aqueous saturated sodium hydrogen sulfite, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain 6.67 g of Compound (e).

Workup

  1. customthe resulting reaction mixture
  2. temperaturewas carefully heated
  3. stirringstirred at 50° C. for 4 hours
  4. extractionthe reaction mixture was extracted three times with ether
  5. washwashed with aqueous saturated sodium hydrogen sulfite
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-f03a97a4a3344ae59edc0baf9053a4fa
Source dataset
uspto-grants-2006_07
Patent number
US07070838B2

Reaction notes

Loading…