Ammonium Chloride → HCID 67460492, compound

HRID 554518Notes

Reaction equation

HRID 554518 reaction equation
[CH2:1]([O:8][C:9]1[C:16]([CH3:17])=[CH:15][CH:14]=[CH:13][C:10]=1[CH:11]=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:18][O:19][C:20]1[CH:25]=[CH:24][C:23]([Mg]Br)=[CH:22][CH:21]=1.[Cl-].[NH4+]>C1COCC1>[CH2:1]([O:8][C:9]1[C:16]([CH3:17])=[CH:15][CH:14]=[CH:13][C:10]=1[CH:11]([C:23]1[CH:24]=[CH:25][C:20]([O:19][CH3:18])=[CH:21][CH:22]=1)[OH:12])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 110641372-benzyloxy-3-methylbenzaldehydeHCID 178491912HCID 178491912, compound

Product 1

HCID 67460492HCID 67460492, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

In a nitrogen stream, to a solution of 2-benzyloxy-3-methyl-benzaldehyde (1.87 g, 8.25 mmol) in THF (50 mL), a solution of 4-methoxyphenylmagnesium bromide in THF (0.5 M, 19.8 mL) was added dropwise under cooling with ice. The mixture was stirred at room temperature for one hour, and then a saturated ammonium chloride aqueous solution was added thereto under cooling with ice 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. The obtained residue was purified by silica gel column chromatography [developing solution=ethyl acetate: n-hexane (1:5)] to obtain the title compound (2.76 g, 100%).

Workup

  1. temperatureunder cooling with ice
  2. temperatureunder cooling with ice
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with a saturated sodium chloride aqueous solution
  5. dry with materialdried (anhydrous magnesium sulfate)
  6. distillationthe solvent was distilled under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography [developing solution=ethyl acetate: n-hexane (1:5)]

Sources & evidence

ORD record
ord-8491c81725904f33b41bb1644ca50c39
Source dataset
uspto-grants-2011_11
Patent number
US08048897B2

Reaction notes

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