Hydrochloric Acid → HCID 14275054, compound

HRID 554530Notes

Reaction equation

HRID 554530 reaction equation
CCCCCC.C([Li])CCC.C([O:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1Br)C1C=CC=CC=1.[CH3:27][O:28][C:29]1[CH:30]=[C:31]([CH:34]=[CH:35][C:36]=1[O:37][CH3:38])[CH:32]=O.[Cl-].[NH4+].Cl>C1COCC1.CO.[OH-].[Pd+2].[OH-]>[CH3:27][O:28][C:29]1[CH:30]=[C:31]([CH:34]=[CH:35][C:36]=1[O:37][CH3:38])[CH2:32][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=1[OH:19]

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 8419VeratraldehydeHCID 25517Ammonium ChlorideHCID 5618281-(Benzyloxy)-2-bromobenzeneHCID 178418244HCID 178418244, compound

Product 1

HCID 14275054HCID 14275054, compoundYield 44.4%

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

In a nitrogen stream, an n-butyllithium hexane solution (1.59 M, 4.4 mL) was added dropwise to a solution of 1-benzyloxy-2-bromobenzene (1.74 g, 6.61 mmol) in THF (30 mL) at −78° C. and the mixture solution was stirred at the same temperature for one hour. To this solution, a solution of 3,4-dimethoxybenzaldehyde (1.00 g, 6.02 mmol) in THF (8 mL) was added dropwise at −78° C. The reaction mixture was stirred at the same temperature for 1.5 hours, and then a saturated ammonium chloride aqueous solution was added thereto and the mixture was extracted with ethyl acetate. The organic layer was washed with a saturated sodium chloride aqueous solution and dried (anhydrous magnesium sulfate), and then the solvent was distilled under reduced pressure to obtain a crude product (2.38 g). The obtained crude product was dissolved in methanol (20 mL) and a 20% palladium hydroxide catalyst (196 mg) was added and furthermore 2N—HCl (30 μL) was added thereto. The mixture solution was stirred under a hydrogen atmosphere for 23 hours, and then the catalyst was filtered off. The solvent was distilled under reduced pressure and the obtained residue was purified by silica gel column chromatography [developing solution=ethyl acetate:n-hexane (1:5)] to obtain the title compound (653 mg, 44%).

Workup

  1. stirringThe reaction mixture was stirred at the same temperature for 1.5 hours
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with a saturated sodium chloride aqueous solution
  4. dry with materialdried (anhydrous magnesium sulfate)
  5. distillationthe solvent was distilled under reduced pressure
  6. customto obtain a crude product (2.38 g)
  7. customThe obtained crude product
  8. stirringThe mixture solution was stirred under a hydrogen atmosphere for 23 hours
  9. filtrationthe catalyst was filtered off
  10. distillationThe solvent was distilled under reduced pressure
  11. customthe obtained residue was purified by silica gel column chromatography [developing solution=ethyl acetate:n-hexane (1:5)]

Sources & evidence

ORD record
ord-0277ec4fabd14eba8a32c7e4a99d4d6a
Source dataset
uspto-grants-2011_11
Patent number
US08048897B2

Reaction notes

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