Methanol → HCID 21905685, compound

HRID 508579Notes

Reaction equation

HRID 508579 reaction equation
[F:1][C:2]([F:13])([F:12])[O:3][C:4]1[CH:11]=[CH:10][C:7](C=O)=[CH:6][CH:5]=1.C(Br)(Br)Br.C[OH:19].[OH-].[K+].CO.[O:24]1[CH2:29][CH2:28][O:27][CH2:26]C1>>[CH3:26][O:27][CH:28]([C:7]1[CH:6]=[CH:5][C:4]([O:3][C:2]([F:1])([F:12])[F:13])=[CH:11][CH:10]=1)[C:29]([OH:24])=[O:19]

Participants

6

Reactant 5

HCID 887MethanolHCID 5558BromoformHCID 14797Potassium HydroxideHCID 69573p-(Trifluoromethoxy)benzaldehydeHCID 21966525Dioxane Methanol

Product 1

HCID 21905685HCID 21905685, compound

Procedure

4-Trifluoromethoxybenzaldehyde (25.0 g) was dissolved in a 1:1 mixed solution of methanol/1,4-dioxane (500 mL), and bromoform (30.3 g) was added thereto under ice cooling. Subsequently, a methanol solution (150 mL) of potassium hydroxide (3.3 g) was added dropwise thereto, and the mixture was stirred for 22 hours at room temperature. After distilling off the solvent under reduced pressure, the residue was diluted with water. The mixture was acidified with 3 mol/L hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with saturated brine and then dried over anhydrous sodium sulfate. After distilling off the solvent under reduced pressure, the residue was purified by silica gel column chromatography (50% to 100% ethyl acetate/hexane), and the title compound (29.4 g) was obtained as a crude product.

Workup

  1. additionwas added
  2. distillationAfter distilling off the solvent under reduced pressure
  3. additionthe residue was diluted with water
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationAfter distilling off the solvent under reduced pressure
  8. customthe residue was purified by silica gel column chromatography (50% to 100% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-15d1b851985a438c90c6e59960ef6432
Source dataset
uspto-grants-2015_08
Patent number
US09096531B2

Reaction notes

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