Triethylamine → 2-methoxy-4-(trifluoromethyl)phenol

HRID 2359298Notes

Reaction equation

HRID 2359298 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:8]=[CH:7][C:4]=1C=O.ClC1C=C(C=CC=1)C(OO)=[O:20].C(N(CC)CC)C>ClCCl>[CH3:1][O:2][C:3]1[CH:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:8]=[CH:7][C:4]=1[OH:20]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 70297m-Chloroperbenzoic acidHCID 49847042-Methoxy-4-(trifluoromethyl)benzaldehyde

Product 1

HCID 102197662-methoxy-4-(trifluoromethyl)phenolYield 57%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-methoxy-4-(trifluoromethyl)benzaldehyde (1.0 g, 4.90 mmol) in dichloromethane (15 mL) was added m-chloroperoxybenzoic acid (1.48 g, 6.61 mmol). The resulting clear solution was stirred for 16 hours at room temperature. Overnight a white precipitate had formed that was filtered off. The filtrate was evaporated to a white solid, which was dissolved in ethyl acetate (25 mL) and washed with saturated aqueous sodium bicarbonate. The organic layer was dried over sodium sulphate, and evaporated to a white solid. This solid was redissolved in methanol (15 mL), and treated with triethylamine (2 mL, 10 mmol). After stirring for two hours, the mixture was concentrated in vacuo. The residue was taken up in ethyl acetate (25 mL), and washed with 1N citric acid solution (20 mL) and brine (20 mL). The organic layer was dried over sodium sulphate, and evaporated to an oil. This crude material was then purified by eluting through a short pad of silica with dichloromethane, which afforded the title compound as a clear oil (536 mg, 57%)

Workup

  1. customOvernight a white precipitate had formed
  2. filtrationthat was filtered off
  3. customThe filtrate was evaporated to a white solid, which
  4. dissolutionwas dissolved in ethyl acetate (25 mL)
  5. washwashed with saturated aqueous sodium bicarbonate
  6. dry with materialThe organic layer was dried over sodium sulphate
  7. customevaporated to a white solid
  8. dissolutionThis solid was redissolved in methanol (15 mL)
  9. stirringAfter stirring for two hours
  10. concentrationthe mixture was concentrated in vacuo
  11. washwashed with 1N citric acid solution (20 mL) and brine (20 mL)
  12. dry with materialThe organic layer was dried over sodium sulphate
  13. customevaporated to an oil
  14. customThis crude material was then purified
  15. washby eluting through a short pad of silica with dichloromethane, which

Sources & evidence

ORD record
ord-d8e5de1b993241fba4ee96954f9ccfd1
Source dataset
uspto-grants-2014_04
Patent number
US08685977B2

Reaction notes

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