Water → HCID 68873227, compound

HRID 1826648Notes

Reaction equation

HRID 1826648 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-ehtylbenzyl)-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. Water was added to the reaction mixture, 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). The resulting solution was added to a suspension of lithium aluminium hydride (0.57 g) in diethyl ether (50 mL) at 0° C., and the mixture was heated under reflux for 1.5 hours. The reaction mixture was cooled to 0° C., water (0.60 mL), 15% aqueous sodium hydroxide solution (0.60 mL) and water (1.8 mL) were successively added to the reaction mixture, and the mixture was stirred for 5 minutes. An insoluble material was 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 resulting solution was added to a suspension of lithium aluminium 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. temperatureThe reaction mixture was cooled to 0° C.
  10. additionwater (0.60 mL), 15% aqueous sodium hydroxide solution (0.60 mL) and water (1.8 mL) were successively added to the reaction mixture
  11. stirringthe mixture was stirred for 5 minutes
  12. customAn insoluble material was removed by filtration
  13. customthe solvent of the filtrate was removed under reduced pressure
  14. customThe residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=2/1)

Sources & evidence

ORD record
ord-05a9f51e913445fe9464698b1b6e0191
Source dataset
uspto-grants-2006_05
Patent number
US07053060B2

Reaction notes

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