2,4-Dihydroxybenzaldehyde → HCID 86709375, compound

HRID 2172192Notes

Reaction equation

HRID 2172192 reaction equation
C(=O)([O-])[O-].[K+].[K+].[F:7][C:8]([F:18])([F:17])[C:9]1[CH:16]=[CH:15][C:12]([CH2:13]Br)=[CH:11][CH:10]=1.[OH:19][C:20]1[CH:27]=[C:26]([OH:28])[CH:25]=[CH:24][C:21]=1[CH:22]=[O:23]>CC(C)=O>[OH:19][C:20]1[CH:27]=[C:26]([O:28][CH2:13][C:12]2[CH:15]=[CH:16][C:9]([C:8]([F:18])([F:17])[F:7])=[CH:10][CH:11]=2)[CH:25]=[CH:24][C:21]=1[CH:22]=[O:23]

Participants

5

Reactant 3

HCID 72132,4-DihydroxybenzaldehydeHCID 11430Potassium CarbonateHCID 1230621-(Bromomethyl)-4-(trifluoromethyl)benzene

Product 1

HCID 86709375HCID 86709375, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Potassium carbonate (16.51 g) and 4-trifluoromethylbenzylbromide (18.47 ml) were added to an acetone solution of 2,4-dihydroxybenzaldehyde (15 g). The mixture was stirred at room temperature for 15 hours and further stirred at 60° C. for 7 hours. After being cooled to room temperature, the mixture was concentrated under reduced pressure. Water was added to the residue, followed by extraction with ethyl acetate. The organic layer was washed with water and a saturated sodium chloride aqueous solution, dried over sodium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1) to afford the title compound as a white powder (12.76 g).

Workup

  1. stirringfurther stirred at 60° C. for 7 hours
  2. temperatureAfter being cooled to room temperature
  3. concentrationthe mixture was concentrated under reduced pressure
  4. additionWater was added to the residue
  5. extractionfollowed by extraction with ethyl acetate
  6. washThe organic layer was washed with water
  7. dry with materiala saturated sodium chloride aqueous solution, dried over sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1)

Sources & evidence

ORD record
ord-5bd8433c89b84fd298047f3252d6a2cd
Source dataset
uspto-grants-2015_06
Patent number
US09051333B2

Reaction notes

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