Reaction #2069982

Reaction equation

ammonium chloride

methyl 4-formyl-3-hydroxybenzoate

1-bromo-4-ethylbenzene

n-pentane

→

diphenylmethanol

Solvents

water

tetrahydrofuran

tetrahydrofuran

Conditions

Workup

1. 1
   workup.STIRRINGAfter the mixture was stirred under ice-
2. 2
   Temperaturecooling for 45 minutes
3. 3
   Extractionthe mixture was extracted with ethyl acetate
4. 4
   WashThe extract was washed with water
5. 5
   Dryingdried over anhydrous magnesium sulfate
6. 6
   Otherthe solvent was removed under reduced pressure
7. 7
   OtherThe residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=3/1)

Procedure

To a solution of 1-bromo-4-ethylbenzene (0.41 mL) in tetrahydrofuran (15 mL) was added 1.45 mol/L tert-buthyllithium n-pentane solution (2.3 mL) under an argon atmosphere at −78° C. After the mixture was stirred at −78° C. for 10 minutes, a solution of methyl 4-formyl-3-hydroxybenzoate (0.18 g) in tetrahydrofuran (5 mL) was added to the reaction mixture. After the mixture was stirred under ice-cooling for 45 minutes, a saturated aqueous ammonium chloride solution and water were added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=3/1) to give a diphenylmethanol compound (0.27 g). The obtained diphenylmethanol compound (0.27 g) was dissolved in methanol (5 mL), and concentrated hydrochloric acid (0.08 mL) and 10% palladium-carbon powder (54 mg) were added to the solution. After the mixture was stirred under a hydrogen atmosphere at room temperature for 18 hours, the catalyst was removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=3/1) to give methyl 4-(4-ethylbenzyl)-3-hydroxybenzoate (0.20 g).

Source