Water → HCID 68873227, compound

HRID 1982846Notes

Reaction equation

HRID 1982846 reaction equation
[CH2:1]([C:3]1[CH:20]=[CH:19][C:6]([CH2:7][C:8]2[CH:17]=[CH:16][C:11]([C:12]([O:14]C)=O)=[CH:10][C:9]=2[OH:18])=[CH:5][CH:4]=1)[CH3:2].C(=O)([O-])[O-].[K+].[K+].[CH2:27](Br)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.O>CN(C)C=O>[CH2:27]([O:18][C:9]1[CH:10]=[C:11]([CH:16]=[CH:17][C:8]=1[CH2:7][C:6]1[CH:5]=[CH:4][C:3]([CH2:1][CH3:2])=[CH:20][CH:19]=1)[CH2:12][OH:14])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 21909266HCID 21909266, compound

Product 1

HCID 68873227HCID 68873227, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of methyl 4-(4-ethylbenzyl)-3-hydroxybenzoate (1.3 g) in N,N-dimethylformamide (15 mL) were added potassium carbonate (0.79 g) and benzyl bromide (0.62 mL), and the mixture was stirred at room temperature for 13 hours. To the reaction mixture was added water, and the mixture was extracted with diethyl ether. The organic layer was washed with water and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue was dissolved in diethyl ether (10 mL), and the solution was added to a suspension of lithium aluminum hydride (0.57 g) in diethyl ether (50 mL) at 0° C. The mixture was heated under reflux for 1.5 hours. After cooling to 0° C., to the reaction mixture was successively added water (0.60 mL), 15% aqueous sodium hydroxide solution (0.60 mL) and water (1.8 mL), and the mixture was stirred for 5 minutes. Insoluble materials were removed by filtration, and the solvent of the filtrate was removed under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=2/1) to give 3-benzyloxy-4-(4-ethylbenzyl)benzyl alcohol (1.3 g).

Workup

  1. extractionthe mixture was extracted with diethyl ether
  2. washThe organic layer was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was removed under reduced pressure
  5. dissolutionThe residue was dissolved in diethyl ether (10 mL)
  6. additionthe solution was added to a suspension of lithium aluminum hydride (0.57 g) in diethyl ether (50 mL) at 0° C
  7. temperatureThe mixture was heated
  8. temperatureunder reflux for 1.5 hours
  9. temperatureAfter cooling to 0° C., to the reaction mixture
  10. stirringthe mixture was stirred for 5 minutes
  11. customInsoluble materials were removed by filtration
  12. customthe solvent of the filtrate was removed under reduced pressure
  13. customThe residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=2/1)

Sources & evidence

ORD record
ord-71384d0e7a0e4a3d9b6b5fdf1efc7542
Source dataset
uspto-grants-2009_06
Patent number
US07541341B2

Reaction notes

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